Methanol → 2,3-Difluoro-6-(hydroxymethyl)phenol

HRID 602066

Reaction equation

HRID 602066 reaction equation
[F:1][C:2]1[C:3]([OH:12])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5](O)=[O:6].S(C)C.CO>C1COCC1>[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:4]([CH2:5][OH:6])[C:3]=1[OH:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 27582863,4-Difluoro-2-hydroxybenzoic acid

Product 1

HCID 451191042,3-Difluoro-6-(hydroxymethyl)phenolYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4-difluoro-2-hydroxy benzoic acid (3.2 g 18.39 mmol) in THF (20 mL) was added BH3.Me2S (7 mL 73.56 mmol) drop wise, over a period of 20 min. at RT. The reaction mixture was stirred at RT for 3 h and monitored by TLC. Methanol (20 mL) was added and the solvent was removed under vacuum. The crude compound was purified by column chromatography over silica gel using a mixture of ethyl acetate and hexane (20:80) as eluent to give the alcohol (2.7 g, 91% yield) MS: m/z 159 (M+1).

Workup

  1. customthe solvent was removed under vacuum
  2. customThe crude compound was purified by column chromatography over silica gel using
  3. additiona mixture of ethyl acetate and hexane (20:80) as eluent

Sources & evidence

ORD record
ord-a2feb40b64ad4e109c672ebbd701c6e6
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Linked notes

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