(Dimethyl sulfide)trihydroboron → 2-(3-(Bromomethyl)-5-methylphenyl)ethanol

HRID 446402Notes

Reaction equation

HRID 446402 reaction equation
CSC.B.[Br:5][CH2:6][C:7]1[CH:8]=[C:9]([CH2:14][C:15](O)=[O:16])[CH:10]=[C:11]([CH3:13])[CH:12]=1>C1COCC1>[Br:5][CH2:6][C:7]1[CH:8]=[C:9]([CH2:14][CH2:15][OH:16])[CH:10]=[C:11]([CH3:13])[CH:12]=1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 581686112-(3-(Bromomethyl)-5-methylphenyl)acetic acid

Product 1

HCID 581684572-(3-(Bromomethyl)-5-methylphenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane dimethyl sulfide complex (2M in THF, 8.6 mL) was added dropwise to a solution of 2-(3-(bromomethyl)-5-methylphenyl)acetic acid [Aromatic Intermediate 23, step a] (2.1 g) in THF (50 mL) at 0° C. and the mixture stirred for 10 minutes at this temperature and then at room temperature for 1 hour. The reaction mixture was quenched by dropwise addition of methanol, the solvents were evaporated under reduced pressure and the residue was purified by flash silica chromatography using 30% ethyl acetate in isohexane as solvent. Fractions containing the product were evaporated to dryness to afford the titled compound. Yield 1.40 g.

Workup

  1. waitat room temperature for 1 hour
  2. customThe reaction mixture was quenched by dropwise addition of methanol
  3. customthe solvents were evaporated under reduced pressure
  4. customthe residue was purified by flash silica chromatography
  5. additionFractions containing the product
  6. customwere evaporated to dryness

Sources & evidence

ORD record
ord-96fce4f098da412d97cd20d632fa4289
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

Loading…