2,6-Difluorophenylacetic acid → 2-(2,6-Difluorophenyl)ethan-1-ol

HRID 471077

Reaction equation

HRID 471077 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)ethan-1-ol

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-eb2c5d41310645ca8883a1856a04ea2f
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Linked notes

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