3-Bromo-5-fluorobenzaldehyde → (3-Bromo-5-fluorophenyl)methanol

HRID 1634993Notes

Reaction equation

HRID 1634993 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=[O:6]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][OH:6]

Participants

3

Reactant 1

HCID 219862463-Bromo-5-fluorobenzaldehyde

Product 1

HCID 2769402(3-Bromo-5-fluorophenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-bromo-5-fluorobenzaldehyde(22.25 g, 0.11 mole) in methanol at rt was added NaBH4,(2.07 g, 0.055 mole) stirred at rt for 2 hr. The reaction was quenched with H2O, and concentrated. The residue was diluted with diethyl ether, washed with 1 N HCl, brine, dried over MgSO4, and concentrated. 3-Bromo-5-fluorobenzyl alcohol was obtained as a colorless oil was collected (14.6 g, 65%). 1H NMR (DMSO-d6) δ4.50 (m, 2H), 5.44(t, 3H, J=5.93 Hz), 7.16 (dd, 1H, J=1.09, 8.79 Hz), 7.36(s, 1H), 7.38 (dd, 1H, J=2.99, 6.15 Hz); Anal. Calc. For C7H6Br2FO: C, 41.01, H, 2.95. Found: C, 41.30, H, 3.01.

Workup

  1. customThe reaction was quenched with H2O
  2. concentrationconcentrated
  3. additionThe residue was diluted with diethyl ether
  4. washwashed with 1 N HCl, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dfe5da03626f4c8fb0fc4dc110f33be8
Source dataset
uspto-grants-2003_01
Patent number
US06509334B1

Reaction notes

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