Benzyl Bromide → Benzaldehyde, 2-fluoro-3-(phenylmethoxy)-

HRID 1582637Notes

Reaction equation

HRID 1582637 reaction equation
[F:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[F:1][C:2]1[C:9]([O:10][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5877892-Fluoro-3-hydroxybenzaldehyde

Product 1

HCID 561331Benzaldehyde, 2-fluoro-3-(phenylmethoxy)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-3-hydroxybenzaldehyde (16.49 g) was dissolved in dimethylformamide (200 ml) and stirred under an argon atmosphere. Sodium hydride was added (60% in mineral oil, 5.18 g) and the mixture was stirred for 30 minutes. Benzyl bromide was added (16.8 ml) and the mixture was stirred overnight. Reaction mixture was concentrated in vacuo and the resulting residue was partitioned between diethyl ether (200 ml) and water (200 ml). Combined organic extracts were washed with water (400 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography, using a gradient of 0-10% ethyl acetate/iso-hexane as eluent to give the product as a yellow solid (18.41 g) 1H NMR (DMSO-d6) δ 5.20(s, 2H), 7.2-7.6(m, 8H), 10.21(s, 1H)

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. stirringthe mixture was stirred overnight
  3. customReaction mixture
  4. concentrationwas concentrated in vacuo
  5. customthe resulting residue was partitioned between diethyl ether (200 ml) and water (200 ml)
  6. washCombined organic extracts were washed with water (400 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-6ab7ebf8c70946518e77e3cc89b83c8c
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

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