Water → 2-(Benzyloxy)-3-fluorobenzaldehyde

HRID 439564Notes

Reaction equation

HRID 439564 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[OH:12].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C)C=O.C(OCC)C>[CH2:13]([O:12][C:5]1[C:4]([F:3])=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5877883-Fluorosalicylaldehyde

Product 1

HCID 224116702-(Benzyloxy)-3-fluorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (688 mg, 28.7 mmol) in dimethylformamide (20 ml) on ice bath was bit by bit added 3-fluorosalicylaldehyde (2.68 g, 19.1 mmol) with stirring. After dropwise adding benzyl bromide (2.73 ml, 22.9 mmol), the mixture was stirred under ice cooling for 30 minutes, stirred at room temperature for 2 hours, mixed with water and the product was shaken with diethyl ether (60 ml×2). The extracts were washed with 10% aqueous sodium carbonate solution, dilute hydrochloric acid and water in this order, dried over anhydrous magnesium sulfate and concentrated in vacuo to remove the solvent to give 2-benzyloxy-3-fluorobenzaldehyde as an oily material.

Workup

  1. stirringstirred at room temperature for 2 hours
  2. washThe extracts were washed with 10% aqueous sodium carbonate solution, dilute hydrochloric acid and water in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto remove the solvent

Sources & evidence

ORD record
ord-c3ee7b0c926748faae86324478525bde
Source dataset
uspto-grants-1996_05
Patent number
US05514711

Reaction notes

Loading…