Tetrahydrofuran → (4-Bromo-2-methylphenyl)methanol

HRID 2247767Notes

Reaction equation

HRID 2247767 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([CH3:11])[CH:3]=1.O1CCCC1>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([CH3:11])[CH:3]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22280088(4-Bromo-2-methylphenyl)methanol

Procedure

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 24 (24e) using 4-bromo-2-methylbenzoic acid (4.0 g, 19 mmol) and a 1.0 M solution of borane-tetrahydrofuran complex in tetrahydrofuran (20 ml, 20 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:19 to 3:2) as the eluent to afford the title compound (3.7 g) in a yield of 99% as a colourless oily product.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-c71a3f5b952b486992686966fbc2e731
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

Loading…