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

HRID 252114

Reaction equation

HRID 252114 reaction equation
B.C1COCC1.[Br:7][C:8]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11]>C1COCC1>[Br:7][C:8]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:9]=1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 331262-Bromo-4-chlorobenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 54049764(2-Bromo-4-chlorophenyl)methanolYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add borane-THF (1 M in THF, 3.2 mL) complex dropwise to an ice-cooled solution of 2-bromo-4-chlorobenzoic acid (500 mg, 2.1 mmol) in THF (2 mL). Remove the cooling bath and stir overnight. Slowly add water (1 mL) and solid sodium carbonate. Stir 1 h. Filter and wash solids with THF. Chromatograph on silica gel, eluting with 0:100 to 30:70 ethyl acetate:dichloromethane to give 2-bromo-4-chlorobenzyl alcohol as a white solid (378 mg, 80%).

Workup

  1. customRemove the cooling bath
  2. stirringStir 1 h
  3. filtrationFilter
  4. washwash solids with THF
  5. washChromatograph on silica gel, eluting with 0:100 to 30:70 ethyl acetate

Sources & evidence

ORD record
ord-99fc7593d3714863940340fb8582927e
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Linked notes

Loading…