Hydrochloric Acid → HCID 87806978, compound

Participants

Reaction Conditions

Reaction Steps

Hexamethylenetetramine (262 mg, 1.87 mmol) was added to a solution of methyl[3,5-dibromo-4-(4-hydroxyphenoxy)phenyl]acetate (370 mg, 0.89 mmol) and trifluoroacetic acid (1.5 mL). The reaction mixture was stirred for 16 hours at 95° C. before cooling to room temperature. Hydrochloric acid (3 mL, 2 N) was added and the reaction mixture was stirred for one hour and extracted with chloroform. The organic phase was concentrated in vacuo and dissolved in ethyl acetate. The organic phase was washed with hydrochloric acid (2 N), water and brine, dried over Na2SO4 and concentrated. The residue was purified on a column (MPLC, silica, gradient eluent: n-heptane/ethyl acetate from 1:0 to 4:1) to give yielded methyl[3,5-dibromo-4-(3-formyl-4-hydroxyphenoxy)phenyl]acetate as a white solid (150 mg, 38%).

Provenance & Evidence