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

HRID 1689330Notes

Reaction equation

HRID 1689330 reaction equation
B.CSC.[Br:5][CH2:6][C:7]1[CH:8]=[C:9]([CH2:14][C:15](O)=[O:16])[CH:10]=[C:11]([Cl: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]([Cl:13])[CH:12]=1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 579893592-(3-(Bromomethyl)-5-chlorophenyl)acetic acid

Product 1

HCID 579892922-(3-(Bromomethyl)-5-chlorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane-methyl sulfide complex (2 M in THF, 2.8 mL) was added portionwise over 5 minutes to a solution of 2-(3-(bromomethyl)-5-chlorophenyl)acetic acid (example 52, step a) (0.73 g) in dry THF (10 mL) at room temperature. The resulting effervescing solution was stirred for 1 hour, then cooled in ice-water and quenched by the portionwise addition of methanol (3 mL) over 5 minutes. The solution was stirred at room temperature for a further 20 minutes and then concentrated in vacuo. The residue was purified by flash chromatography on silica eluted with 25% ethyl acetate in isohexane to afford the crude subtitled compound as a white solid. Yield 0.46 g.

Workup

  1. customquenched by the portionwise addition of methanol (3 mL) over 5 minutes
  2. stirringThe solution was stirred at room temperature for a further 20 minutes
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica
  5. washeluted with 25% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-afa91715d3e24bbd8410d4e2c3a41c9c
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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