4-[(2,5-difluorophenyl)methoxy]benzaldehyde synthesis

Yield:1272111-71-3 71%

Reaction Conditions:

Stage #1: 4-hydroxy-benzaldehydewith potassium tert-butylate in dimethyl sulfoxide at 5 - 10; for 0.666667 h;
Stage #2: 2-(bromomethyl)-1,4-difluorobenzene in dimethyl sulfoxide at 5 - 20;

Steps:

6.2. General procedure for the synthesis of compounds 2a-f and 14a-f

General procedure: To a stirred suspension of 4-hydroxy benzaldehyde/4-hydroxy acetophenone (1 mmol) in dimethyl sulfoxide (DMSO) (5 mL) at 5-10 °C was added potassium t-butoxide (1.2 mmol) was added in small portions in the period of 10 min. After stirring of 30 min, substituted benzyl/aryl halide (1 mmol) was added and then stirring was continued at room temperature for 4-5 h. The reaction mixture was quenched with ice cold water (5 mL) and extracted with ethyl acetate (3 × 5 mL), the combined organic layers were washed with water (3 × 5 mL) dried over Na₂SO₄ and concentrated under reduced pressure to obtain the crude product which was purified by column chromatography by using silica gel (60-120 mesh) and ethyl acetate: Hexane (4:94) as eluent to give the compounds (2a-f and 14a-f).

References:

Marrapu, Vijay K.;Chaturvedi, Vinita;Singh, Shubhra;Singh, Shyam;Sinha, Sudhir;Bhandari, Kalpana [European Journal of Medicinal Chemistry,2011,vol. 46,# 9,p. 4302 - 4310] Location in patent:experimental part