2,3-Difluorophenol synthesis
- Product Name:2,3-Difluorophenol
- CAS Number:6418-38-8
- Molecular formula:C6H4F2O
- Molecular Weight:130.09
121219-16-7
6418-38-8
Step 1: In a 500 mL round-bottomed flask, dissolve 2,3-difluorophenylboronic acid (30 g, 189.98 mmol, 1.00 eq.) in dichloromethane (250 mL). Hydrogen peroxide (30 mL) was added slowly and dropwise under stirring conditions. The reaction mixture was stirred continuously at 25°C for 2 hours. Upon completion of the reaction, the reaction mixture was washed sequentially with water and saturated saline, the organic phase was dried over anhydrous magnesium sulfate, and subsequently concentrated under reduced pressure to afford 2,3-difluorophenol 23 g (93% yield) as a brown oil.
367-11-3
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6418-38-8
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Yield:6418-38-8 96.49%
Reaction Conditions:
Stage #1:ortho-difluorobenzene with n-butyllithium in tetrahydrofuran at -78; for 1 h;
Stage #2: with Trimethyl borate in tetrahydrofuran for 16 h;
Stage #3: with dihydrogen peroxide in tetrahydrofuran for 3 h;
Steps:
1.c.1 Step 1:
To a suspension of 1 ,2-difluorobenzene (20.0 g, 175.4 mmol, 1.0 eq) in dry THF (250 mL), cooled to -78°C, n-BuLi (80 mL, 1.1 eq, 1.6 M) was added dropwise, then the reaction mass stirred at -78°C for 1 h. After 1 h, the reaction was quenched with trimethylborate (30.0 mL, 263.157 mmol, 1 .5 eq) then stirred for 16 h. TLC analysis indicated a polar spot. The reaction was then quenched with 30% hydrogen peroxide solution (80 mL) then stirred for 3 h. TLC analysis indicated a non-polar spot. The reaction mixture was extracted with diethyl ether (1 L) and washed with water (500 mL) The separated organic layer was dried over Na2S04 and concentrated under reduced pressure to give the desired 2,3-difluorophenol (21 .8 g, 93.96%) as a liquid.
References:
ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR);AL-AWAR, Rima;ISAAC, Methvin;CHAU, Anh My;MAMAI, Ahmed;WATSON, Iain;PODA, Gennady;SUBRAMANIAN, Pandiaraju;WILSON, Brian;UEHLING, David WO2019/119145, 2019, A1 Location in patent:Paragraph 00210
121219-16-7
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6418-38-8
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6418-38-8
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6418-38-8
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