Methanol → 4-(Bromomethyl)benzeneethanol

HRID 1689229Notes

Reaction equation

HRID 1689229 reaction equation
CSC.B.[Br:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](O)=[O:15])=[CH:9][CH:8]=1.CO>C1COCC1>[Br:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 45190564-(Bromomethyl)phenylacetic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 223370184-(Bromomethyl)benzeneethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane dimethylsulphide complex (2M in THF, 4.37 mL) was added dropwise to a solution of 2-(4-(bromomethyl)phenyl)acetic acid (1.0 g) in THF (20 mL) at 20° C. and the mixture stirred for 1 hour. Methanol was added dropwise until bubbling ceased and the solvent evaporated in vacuo. Purification was by silica gel chromatography eluting with 30% ethyl acetate in isohexane. The fractions containing product were combined and evaporated in vacuo to give the subtitled compound as a white crystalline solid. Yield 0.86 g.

Workup

  1. customuntil bubbling
  2. customthe solvent evaporated in vacuo
  3. customPurification
  4. washeluting with 30% ethyl acetate in isohexane
  5. additionThe fractions containing product
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-bf7bb4f3ef4143cfbea7df59ed8843f4
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

Loading…