3-Bromo-4-fluorobenzaldehyde → 3-Bromo-4-fluorobenzyl Alcohol

HRID 1627360Notes

Reaction equation

HRID 1627360 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:6].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

4

Reactant 2

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 27733513-Bromo-4-fluorobenzyl AlcoholYield 105.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-bromo-4-fluorobenzaldehyde (50 g, 0.246 mol) in MeOH (500 mL) at 0° C. was added NaBH4 (9.3 g, 0.246 mol) portionwise. After 1 h, the reaction was concentrated in vacuo, diluted with water and extracted with DCM. The combined extracts were dried over MgSO4 and concentrated in vacuo to give (3-bromo-4-fluorophenyl)methanol (53 g). 1H NMR (400 MHz, CDCl3) δ 7.58-7.56 (m, 1H), 7.28-7.25 (m, 1H), 7.09 (t, J=4.4 Hz, 1H), 4.65 (d, J=5.2 Hz, 2H), 1.82 (t, J=5.6 Hz, 1H).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with DCM
  4. dry with materialThe combined extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e6ee90fa9d74437beae04dfa34d95da
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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