Methanol → 2-Bromo-5-fluorobenzyl alcohol

HRID 240274

Reaction equation

HRID 240274 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[C:4](OC)=[O:5].[BH4-].[Na+].CO.O>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 138875Benzoic acid, 2-bromo-5-fluoro-, methyl esterHCID 4311764Sodium borohydride

Product 1

HCID 27733492-Bromo-5-fluorobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-bromo-5-fluorobenzoate (10, 21.30 g, 91.4 mmol) in dry THF (150 mL) was added NaBH4 (6.95 g, 183 mmol). Methanol (20 mL) was added dropwise at RT. After the addition, the mixture was stirred at RT for 1 h. Water (200 mL) was slowly added. The mixture was extracted with CH2Cl2 (100 mL×2). The combined extracts were washed with saturated NaHCO3 and brine, dried over MgSO4 and concentrated to give (2-bromo-5-fluorophenyl)methanol (11).

Workup

  1. additionAfter the addition
  2. extractionThe mixture was extracted with CH2Cl2 (100 mL×2)
  3. washThe combined extracts were washed with saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f680df50dc154f649f0aca6fe6f78b8d
Source dataset
uspto-grants-2014_02
Patent number
US08648073B2

Linked notes

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