Bromonitromethane → HCID 19800065, compound

Participants

Reaction Conditions

Reaction Steps

2,3,5-Trichlorobenzonitrile (9.7 g, 47 mmol) and 3-mercaptopropionitrile (4.9 g, 56 mmol) (L. Bauer, T.L. Welsh, J. Org. Chem., 1443 (1961)) was dissolved in 130 ml of DMF. The mixture was stirred and cooled to 0° C., flushed with a stream of nitrogen, and 25% potassium hydroxide (20 ml) was added dropwise. When the addition was complete the mixture was stirred for 0.5 h and bromonitromethane (3.92 ml, 56 mmol) was added dropwise. The ice bath was removed and the mixture was stirred for a further 16 h. The mixture was poured into ice-water and the precipitate was isolated, washed with water and dried to afford 10.6 g (86%) of 3-amino-5,7-dichloro-2-nitrobenzo[b]-thiophene M.p. 290°-92° C. 1H-NMR (DMSO-d6): 8.02 (d, 1H), 8.54 (d, 1H), 9.00 (br. s, 1H).

Provenance & Evidence