2,6-Difluorophenylacetic acid → 2-(2,6-Difluorophenyl)ethanol

HRID 1689308Notes

Reaction equation

HRID 1689308 reaction equation
CSC.B.[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[CH2:13][C:14](O)=[O:15]>C1COCC1>[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[CH2:13][CH2:14][OH:15]

Participants

4

Reactant 2

HCID 1235852,6-Difluorophenylacetic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 450906762-(2,6-Difluorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane dimethyl sulfide complex (2M in THF, 26 mL) was added cautiously to a solution of 2-(2,6-difluorophenyl)acetic acid (3 g) in THF (50 mL) at 0° C. The reaction was then allowed to warm to RT and stirred for 3 h. The reaction was cooled in an ice bath and cautiously quenched with methanol (10 mL). The solvent was evaporated and the residue purified by silica gel chromatography eluting with 9:1 to 4:1 isohexane:ethyl acetate gradient. The fractions containing product were combined and evaporated to give the subtitled compound as a clear oil. Yield 2.2 g.

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. customcautiously quenched with methanol (10 mL)
  3. customThe solvent was evaporated
  4. customthe residue purified by silica gel chromatography
  5. washeluting with 9:1 to 4:1 isohexane
  6. additionThe fractions containing product
  7. customevaporated

Sources & evidence

ORD record
ord-bd40ba3cee6a4d8dac0f674f781203fa
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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