Benzyl Bromide → 2-(Benzyloxy)-4-fluorobenzaldehyde

HRID 910840Notes

Reaction equation

HRID 910840 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:17]([O:10][C:4]1[CH:3]=[C:2]([F:1])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27792684-Fluoro-2-hydroxybenzaldehyde

Product 1

HCID 106809572-(Benzyloxy)-4-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the product from step (i) (3.0 g), potassium carbonate (4.42 g) and benzyl bromide (3.90 ml) in DMF (40 ml) was heated at 90° C. for 14 h. The mixture was partitioned between water/ethyl acetate, the organics separated, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with isohexane/diethylether 5:1, yield 6.3 g.

Workup

  1. customThe mixture was partitioned between water/ethyl acetate
  2. customthe organics separated, dried
  3. customevaporated under reduced pressure
  4. customThe residue was purified by chromatography on silica eluting with isohexane/diethylether 5:1, yield 6.3 g

Sources & evidence

ORD record
ord-ddfb20d4666a47638d5756304e640853
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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