3-fluoro-2-phenylmethoxybenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. stirred at room temperature for 2 hours The extracts were washed with 10% aqueous sodium carbonate solution, dilute hydrochloric acid and water in this order dried over anhydrous magnesium sulfate concentrated in vacuo to remove the solvent

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

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). extracted several times with ethyl acetate the organic phase is dried over sodium sulfate concentrated in vacuo dried under high vacuum The crude product is purified by silica gel chromatography (cyclohexane:ethyl acetate 2:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. stirred at room temperature for 2 hours The extracts were washed with 10% aqueous sodium carbonate solution, dilute hydrochloric acid and water in this order dried over anhydrous magnesium sulfate concentrated in vacuo to remove the solvent