3-Hydroxybenzaldehyde → 3-[(2-Fluorobenzyl)oxy]benzaldehyde

HRID 915553Notes

Reaction equation

HRID 915553 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[F:9].[OH:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=[O:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=[O:15]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotoluene

Product 1

HCID 7845823-[(2-Fluorobenzyl)oxy]benzaldehydeYield 9.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

0.5 M solution of 1-bromomethyl-2-fluoro-benzene (1.50 g, 8.0 mmol) in DMF was added dropwise to a suspension of 3-hydroxy-benzaldehyde (0.89 g, 7.3 mmol), K2CO3 (1.51 g, 11 mmol) and KI (0.12 g, 0.73 mmol) in 100 ml DMF. The reaction mixture was stirred at 90° C. overnight. After cooling to room temperature, the solid residue was filtered off and the solvent was evaporated under vacuum. The residue was dissolved in ethyl acetate, the organic layer washed twice with 1M NaOH, dried over Na2SO4 and evaporated to dryness. The residue was purified on silica gel, obtaining 167 mg of the title compound (quantitative yield).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solid residue was filtered off
  3. customthe solvent was evaporated under vacuum
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe organic layer washed twice with 1M NaOH
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-a17f6aca10bc4bb4bca856a2dfbc6bc6
Source dataset
uspto-grants-2007_09
Patent number
US07265244B2

Reaction notes

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