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CAS No. : | 98130-56-4 | MDL No. : | MFCD00070752 |
Formula : | C6H3BrF2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YDRZYJATKMBSJX-UHFFFAOYSA-N |
M.W : | 208.99 | Pubchem ID : | 2736290 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 12h; | A solution of <strong>[98130-56-4]2-bromo-4,6-difluorophenol</strong> (1.00 g, 4.78 mmol) in DMF (25 ml) was treated with potassium carbonate (3.3 g, 23.9 mmol) and t-butyl bromoacetate (0.85 ml, 5.74 mmol) at 60 C. for 12 hours. The reaction mixture was filtered through celite, and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 5-10% ethyl acetate/hexane gradient to afford a white solid (t-butyl ester). This product was treated with 4 N HCl in dioxane (10 ml) at room temperature for 12 hours. The reaction mixture was concentrated, triturated with hexane, and filtered under suction to afford a white solid (0.92 g, 72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium hydroxide; tetrabutylammomium bromide; In tetrahydrofuran; water; at 64℃; for 2h; | 2-Bromo-4,6-difluoro-phenol (10 g, 48 mmol), Bu4NBr (0.24 g, 0.72 mol) and BnBr (8.22 g, 48 mmol) was mixed in THF (100 mL). 50% KOH (13.46 g, 240 mmol) was added to the mixture, heated to 64 C and stirred for 2 h. Water was added to the mixture, the aqueous layer was extracted with EtOAc. The organic layer was washed with brine, dried over Na2Sθ4 and concentrated in vacuo to give the crude product 2- (benzyloxy)-1-bromo-3,5-difluorobenzene (13.7 g, 96%), which was used immediately without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2h; | A mixture of 2-bromo-4,6- difluorophenol (5 g, 23.92 mmol), sodium 2-chloro-2,2-difluoroacetate (4.38 g, 28.7 mmol), and potassium carbonate (3.97 g, 28.7 mmol) in DMF (20 ml) was heated in a 100C oil bath for 2 h. The mixture was diluted with water and methylene chloride. The methylene chloride layer was separated, washed 3 times with water, dried over magnesium sulfate, and concentrated to give 1 -bromo-2- (difluoromethoxy)-3,5-difluorobenzene as a clear oil (5.44 g, 44%). 'H NMR (400MHz, CHLOROFORM-d) δ 7.25 - 7.15 (m, 1H), 6.95 (ddd, J=9.8, 8.0, 3.0 Hz, 1H), 6.79 - 6.33 (m, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17.0 g | With 1H-imidazole; In N,N-dimethyl-formamide; at 10 - 35℃; for 2h; | To a solution of <strong>[98130-56-4]2-bromo-4,6-difluorophenol</strong> (16.1 g) and imidazole (7.85 g) in DMF was added tert-butylchlorodimethylsilane (11.6 g), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with 1N hydrochloric acid, saturated sodium hydrogen carbonate, and saturated brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound (17.0 g). 1H NMR (300 MHz, CDCl3) δ 0.21-0.25 (6H, m), 1.02-1.07 (9H, m), 6.82 (1H, ddd, J = 10.7, 8.1, 3.1 Hz), 7.04-7.11 (1H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | 7cp (212 mg, 1.01 mmol) was dissolved in THF (2.0 mL). This sodium hydride was stirred for 1 hour at (mineral oil suspension, purity 60%, 48 mg, 1.20 mmol) was added thereto at room temperature. The stuff 5 (202 mg, 0.36 mmol) was added THF (2.0 mL) solution of was stirred at room temperature for 24 hours. The reaction solution was diluted with ethyl acetate (10 mL), sequentially washed with water (10 mL) and brine (10 mL). This was filtered and dried over anhydrous sodium sulfate, and concentrated in an evaporator. The obtained residue was purified by silica gel column chromatography (silica gel:. 6 g, developing solvent: ethyl acetate - methanol mixed solvent pair 0 → 45: 1 → 20: 1 →. 8-to-1 → 1: 1) was separated and purified by, 9cp It was obtained (85 mg, 0.14 mmol, 40% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With potassium carbonate; In acetonitrile; at 60℃; for 16h; | To a mixture of <strong>[98130-56-4]2-bromo-4,6-difluorophenol</strong> (10.0 g, 47.85 mmol) and iodoethane (14.9 g, 95.7 mmol) in MeCN (200 mL) was added K2CO3 (13.2 g, 95.7 mmol). The mixture was warmed to about 60 C. and stirred for about 16 h. The mixture was cooled to about 20 C., filtered and the filtrate concentrated. The residue was dissolved in EtOAc (200 mL). The EtOAc layer was washed with water (80 mL), brine (50 mL), dried over MgSO4, filtered and concentrated to afford 1-bromo-2-ethoxy-3,5-difluorobenzene (11.0 g, 97%), which was used in Preparation 195. 1H NMR (CDCl3, 400 MHz): δ 7.09-7.12 (m, 1H), 6.82-6.88 (m, 1H), 4.12 (q, J=7.0 Hz, 2H), 1.43 (t, J=7.0 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.5% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | Example 1.18 To a stirred solution of <strong>[98130-56-4]2-bromo-4,6-difluorophenol</strong> (5.70 g, 1.0 equiv., 27.3 mmol) and ethyl 2-bromo-2,2-difluoroacetate (11.1 g, 2.0 equiv., 54.5 mmol) in DMF (120.0 mL) was added K2CO3 (7.54 g, 2.0 equiv., 54.5 mmol) in portions at room temperature under nitrogen atmosphere. The resulting mixture was stirred overnight at room temperature under nitrogen atmosphere. The mixture was diluted with water (100 mL). The resulting mixture was extracted with EtOAc (3*120 mL). The combined organic layers were washed with brine (2*100 mL), dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford ethyl 2-(2-bromo-4,6-difluorophenoxy)-2,2-difluoroacetate (4.56 g, 50.5%) as an oil. LCMS (ESI): m/z [M+H]+=331.0; 1H NMR (400 MHz, Chloroform-d) δ 7.20-7.24 (m, 1H), 6.93-6.96 (m, 1H), 4.47 (q, J=7.1 Hz, 2H), 1.44 (t, J=7.2 Hz, 3H). |