Lawesson's reagent → HCID 86642943, compound

Participants

Reaction Steps

Step 2 A mixture of N-(3-bromo-2-methylphenyl)-2-fluorobenzamide (2.00 g, 6.49 mmol) and 2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide (Lawesson reagent, 1.575 g, 3.89 mmol) in toluene (25 mL) was heated at reflux. After 3.5 h, the solution was cooled to rt and concentrated to provide a dark yellow solid. This was purified by column chromatography (eluting with a gradient from 95:5 to 90:10 hexane-EtOAc) to provide N-(3-bromo-2-methylphenyl)-2-fluorobenzothioamide as a yellow solid (1.892 g, 90%). 1H NMR (400 MHz, chloroform-d) δ 9.18 (1H, d, J=7.7 Hz), 8.23 (1H, td, J=8.0, 1.8 Hz), 7.60 (1H, d, J=7.9 Hz), 7.45-7.52 (1H, m), 7.43 (1H, d, J=7.7 Hz), 7.23-7.30 (1H, m), 7.11-7.21 (2H, m), 2.41 (3H, s). Mass spectrum m/z 324, 326 (M+H)+.

Provenance & Evidence