Methanol → 2-Bromo-5-fluorobenzyl alcohol

HRID 524107Notes

Reaction equation

HRID 524107 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-1a20cd7cc67744539f203a1ea8f428c8
Source dataset
uspto-grants-2016_05
Patent number
US09340523B2

Reaction notes

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