Water → (4-Bromo-3-methylphenyl)methanol

HRID 1708054Notes

Reaction equation

HRID 1708054 reaction equation
B#B.[Br:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][C:5]=1[CH3:13].O.[OH-].[Na+]>C1COCC1>[Br:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][OH:9])=[CH:6][C:5]=1[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 821314-Bromo-3-methylbenzoic acidHCID 6328200Diboron

Product 1

HCID 10987288(4-Bromo-3-methylphenyl)methanolYield 63.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diborane in THF (1M; 220 ml) was added dropwise to a solution of 4-bromo-3-methylbenzoic acid (20.0 g) in THF (100 ml) at room temperature under nitrogen. The solution was stirred for 5 h, treated cautiously with water (20 ml) and aqueous sodium hydroxide (2N; 200 ml) and extracted with ether (3×100 ml). The dried extract was evaporated to give the title compound as a colourless oil (11.8 g).

Workup

  1. extractionextracted with ether (3×100 ml)
  2. extractionThe dried extract
  3. customwas evaporated

Sources & evidence

ORD record
ord-6f2fa67ae54d4023bb806644e3ea123d
Source dataset
uspto-grants-1994_10
Patent number
US05356893

Reaction notes

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