2-Bromoethanol → 2-[(5-Nitro-2-pyridinyl)thio]ethanol

Participants

Reaction Conditions

Reaction Steps

A heterogeneous mixture of 2-mercapto-5-nitropyridine (4) (0.50 g, 3.2 mmol), 2-bromoethanol (1) (0.238 mL, 3.3 mmol), and K2CO3 (2.0 g, 14 mmol) in acetone (11 mL) was stirred at 55° C. for 1 h. The cooled reaction mixture was filtered through Celite®, concentrated, and then purified by silica gel chromatography to give 2-[(5-nitro-2-pyridinyl)thio]ethanol (7) as an orange solid (0.545 g, 2.72 mmol). 1H NMR (CDCl3): δ 9.20 (d, J=3.0 Hz, 1H), 8.23 (dd, J=3.0 and 8.7 Hz, 1H), 7.36 (d, J=8.7 Hz, 1H), 3.94 (t, J=6.0 Hz, 2H), 3.46 (d, J=6.0 Hz, 2H); LCMS: purity: 96%; MS (m/e): 201(MH+).

Provenance & Evidence