Ethanethiol → (2-Bromo-4-nitrophenyl)(ethyl)sulfane

Participants

Reaction Conditions

Reaction Steps

To 3-bromo-4-fluoronitrobenzene (7.05 g, 32.0 mmol) and ethanethiol (2.6 mL, 35.2 mmol) in DMF (20 mL) was added potassium carbonate (4.87 g, 35.2 mmol). The reaction mixture was heated to 60° C. overnight. After cooling, the mixture was filtered over celite and washed with ethyl acetate. The combined filtrate and washings were concentrated. The residue was redissolved in ethyl acetate and washed with water (3×) and then dried over sodium sulfate. The filtrate was concentrated and purified by flash column chromatography to give 100A (8.09 g, 96% yield) as a solid. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.41 (t, J=7.34 Hz, 3H) 3.11 (q, J=7.42 Hz, 2H) 7.45 (d, J=9.05 Hz, 8H) 8.17 (dd, J=8.80, 2.45 Hz, 7H) 8.37 (d, J=2.45 Hz, 7H).

Provenance & Evidence