Methanol → 2-(3,4-Difluorophenyl)ethan-1-ol

HRID 471033Notes

Reaction equation

HRID 471033 reaction equation
CSC.B.[F:5][C:6]1[CH:7]=[C:8]([CH2:13][C:14](O)=[O:15])[CH:9]=[CH:10][C:11]=1[F:12].CO>C1COCC1>[F:5][C:6]1[CH:7]=[C:8]([CH2:13][CH2:14][OH:15])[CH:9]=[CH:10][C:11]=1[F:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 69571(3,4-Difluorophenyl)acetic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 27583132-(3,4-Difluorophenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane dimethyl sulfide (2M in THF, 18.30 mL) was added cautiously to a solution of 2-(3,4-difluorophenyl)acetic acid (2.1 g) in THF (20 mL) at 0° C. The resulting mixture was allowed to warm to RT and stirred for 1 h. The reaction was cooled in an ice bath and methanol (5 mL) was added dropwise. The reaction was stirred until bubbling ceased and the solvent evaporated in vacuo. Purification was by silica gel chromatography eluting with isohexane to 4:1 isohexane:ethyl acetate. The fractions containing product were combined and evaporated in vacuo to give the subtitled compound as a clear oil. Yield 1.92 g.

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. stirringThe reaction was stirred
  3. customuntil bubbling
  4. customthe solvent evaporated in vacuo
  5. customPurification
  6. washeluting with isohexane to 4:1 isohexane
  7. additionThe fractions containing product
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-ca3c6d18be2e4e908fb1100e720ba073
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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