4-Chlorobenzoyl chloride → HCID 68494851, compound

Participants

Reaction Steps

To a stirred solution of 0.05 g (0.22 mmol) of 15 and 27 uL (0.22 mmol) of 4-chlorobenzoyl chloride in 5 mL of dry CH2Cl2 was added 15 mg (0.11 mmol) of AlCl3 in three portions at room temperature. The resulting mixture was stirred overnight. The reaction mixture was slowly poured onto 5 g of ice and allowed to warm to room temperature. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/Hex 1:9) to give 0.04 g (50%) of [5-(4-chlorobenzoyl)-2-phenylthiophene-3-yl]acetic acid methyl ester as a white solid: 1H NMR (600 MHz, CDCl3) δ 7.84 (d, J=8.2 Hz, 2H), 7.61 (s, 1H), 7.50-7.43 (m, 3H), 3.71 (s, 3H), 3.67 (s, 2H); 13C NMR (150 MHz, CDCl3) δ 186.5, 171.1, 150.1, 140.8, 138.6, 137.3, 136.2, 132.6, 130.5, 129.2, 128.9, 128.8, 128.7, 52.2, 34.1; IR (KBr) cm−1 2949, 1737, 1623; LREIMS C20H15ClO3S requires 370.04. Found: 370 ([M+], 100%), 310 (40%), 139 (59%).

Provenance & Evidence