2,4-Dichlorobenzyl chloride → HCID 57810470, compound

Participants

Reaction Steps

NaH (60% in oil, 526 mg, 13.15 mmol, 1.5 equiv.) was added to a solution of 7-bromo-5-fluoro-3-methyl-1H-indole, [which was prepared analogous to I-30, according to the method of Dobbs, A., J. Org. Chem., 66, 638-641 (2001)], (2 g, 8.77 mmol, 1 equiv.) in DMF (30 mL) at −10° C. Reaction mixture was warmed to rt and stirred for 30 min. A solution of 2,4-dichlorobenzyl chloride (2.06 g, 10.52 mmol, 1.2 equiv.) in DMF (10 mL) was added gradually over 2.5 min at −10° C. The reaction mixture was allowed to warm to rt and stirred for 1 h. The reaction mixture was poured into a stirred solution of 10% HCl/water/ether (1:1:2, 40 mL) mixture, and the aqueous layer was extracted with ether (2×10 mL). The combined organic layers were washed with water (3×75 mL), brine (75 mL), dried over MgSO4, filtered, and concentrated to afford crude product as brown solid. Ether (4 mL) was added to the crude product, cooled down to −78° C. and filtered to afford I-191 (2.49 g, 73%) as off-white solid. 1H-NMR (500 MHz, CDCl3) confirmed the structure.

Provenance & Evidence