Carbon Dioxide → HCID 21071799, compound

Participants

Reaction Steps

To a 25 ml round bottom flask was added 4-(4-methoxyphenyl)-1-benzothiophene (500 mg, 2.08 mmol), CH2Cl2 (10 ml), and the solution was cooled to −20° C. (acetone-water, CO2). Bromine (8.33 ml of 0.25 M stock in CH2Cl2, 2.08 mmol) was slowly added dropwise over 0.5 h and the reaction was stirred for a additional 0.5 h. The reaction was then washed with water, dried over anhydrous Na2SO4, passed through a silica plug and concentrated to 460 mg orange oil. Recrystallization from 3:97 EtOAc-hexanes afforded 350 mg (53%) of product as white crystals: 1H NMR (300 MHz, DMSO-d6): δ 3.83 (3H, s), 7.10 (2H, d, J=8.0 Hz), 7.31 (1H, d, J=7.9 Hz), 7.51 (2H, d, J=8.4 Hz), 7.56 (1H, d, J=5.6 Hz), 7.68 (1H, d, J=7.9 Hz), 7.92 (1H, d, J=5.6 Hz).

Provenance & Evidence