Water → 2-(Benzyloxy)-3-fluorobenzaldehyde

HRID 1441958Notes

Reaction equation

HRID 1441958 reaction equation
[F:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C=O)C>[CH2:17]([O:10][C:3]1[C:2]([F:1])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5877883-Fluorosalicylaldehyde

Product 1

HCID 224116702-(Benzyloxy)-3-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

9.0 g (64 mmol) of 3-fluoro-2-hydroxybenzaldehyde are dissolved in 200 ml of DMF, 10.7 g (77.1 mmol) of potassium carbonate and 8.4 ml (12 g, 71 mmol) of benzyl bromide are added and the mixture stirred at 80° C. for 24 h. The mixture is poured into 600 ml of water, extracted several times with ethyl acetate, and the organic phase is dried over sodium sulfate, concentrated in vacuo and dried under high vacuum. The crude product is purified by silica gel chromatography (cyclohexane:ethyl acetate 2:1).

Workup

  1. extractionextracted several times with ethyl acetate
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customdried under high vacuum
  5. customThe crude product is purified by silica gel chromatography (cyclohexane:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-35349627e539431c8e29463fa0301645
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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