Hydrochloric Acid → 2-Bromo-5-fluorobenzyl alcohol

HRID 1988043Notes

Reaction equation

HRID 1988043 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[Br:11].[BH4-].[Na+].[Li+].[Cl-].Cl>C1COCC1.CCO>[Br:11][C:5]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:4]=1[CH2:3][OH:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 138875Benzoic acid, 2-bromo-5-fluoro-, methyl esterHCID 433294Lithium ChlorideHCID 4311764Sodium borohydride

Product 1

HCID 27733492-Bromo-5-fluorobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The mixture of 2-bromo-5-fluoro-benzoic acid methyl ester (1 g, 4.292 mmol), NaBH4 (0.423 g, 11.159 mmol) and LiCl (0.474 g, 11.159 mmol) in THF/EtOH (20 ml/10 ml) was stirred at room temperature overnight. Aqueous HCl (10 ml, 2N) was added and stirred for about 10 min. Then the organic solvent was removed under low vacuum. The residue was diluted with water and extracted by ethyl acetate. The organic layer was washed with aqueous NaHCO3 (10%), water and brine, and then dried (MgSO4) and concentrated to afford 852 mg (96.8% crude yield) crude product, (2-bromo-5-fluoro-phenyl)methanol, as a white solid, which was used without further purification.

Workup

  1. stirringstirred for about 10 min
  2. customThen the organic solvent was removed under low vacuum
  3. additionThe residue was diluted with water
  4. extractionextracted by ethyl acetate
  5. washThe organic layer was washed with aqueous NaHCO3 (10%), water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8637b1bfcfd142e180158fbc3852ad84
Source dataset
uspto-grants-2009_06
Patent number
US07553840B2

Reaction notes

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