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

HRID 514491Notes

Reaction equation

HRID 514491 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%). 1H NMR (300 MHz, CDCl3): δ 4.72 (2H, s), 7.32 (1H, dd, J=1.8 Hz, 8.1 Hz), 7.43 (1H, d, J=8.1 Hz), 7.56 (1H, d, J=2.1 Hz).

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-5b484bca7f1349c2b15bf3be40ab21b9
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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