2-Bromo-4-chlorobenzoic acid → (2-Bromo-4-chlorophenyl)methanol

HRID 878647Notes

Reaction equation

HRID 878647 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

3

Reactant 1

HCID 331262-Bromo-4-chlorobenzoic acid

Product 1

HCID 54049764(2-Bromo-4-chlorophenyl)methanolYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Added BH3 (1M in THF, 40 mL) to a solution of 2-bromo-4-chlorobenzoic acid (3.14 g, 13.33 mmol) in THF (3 mL) drop wise at 0° C. The reaction mixture was stirred at room temperature overnight. Extracted with ethyl acetate twice, and washed the organic phase with brine and dried with anhydrous Na2SO4, concentrated to give the title compound (2.5 g, 85%).

Workup

  1. extractionExtracted with ethyl acetate twice
  2. washwashed the organic phase with brine
  3. dry with materialdried with anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-52a84b7bcf6b4321b9f9784b92e8d2a0
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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