ChemicalBook CAS DataBase List 2,3-Difluorophenol

2,3-Difluorophenol synthesis

7synthesis methods

Product Name:2,3-Difluorophenol
CAS Number:6418-38-8
Molecular formula:C6H4F2O
Molecular Weight:130.09

367-11-3
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6418-38-8
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$10.00/1g

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

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