Water → HCID 58669195, compound

Participants

Reaction Steps

To an icebath-chilled solution of 3-methyl-4-cyclohexylthiophene (10 g, 55.55 mmol) in DMF (60 mL) was added solid N-bromosuccinimide (9.89 g, 55.55 mmol). After addition, the mixture was allowed to warm to room temperature and was stirred for about 1 hr at which point HPLC analysis indicated the reaction was complete. The product mixture was poured into 200 mL of cold water and the aqueous phase was extracted with ether (3×125 mL). The combined ether extracts were washed with water (3×250 mL) and brine (1×200 mL), then passed through a cone of DRIERITE. Solvent was removed by rotary evaporation to afford the crude product 2-bromo-3-methyl-4-cyclohexylthiophene (13.6 g, 94%) as a light amber oil which was judged to be of greater than 95% purity product. 1H NMR (CDCl3) δ 6.88 (s, 1, ArH), 2.53 (m, 1, cyclohexylmethine) 2.19 (s, 3,ArCH3), 1.9 and 1.35 ppm (m, 10, cyclohexyls).13C NMR 147.81, 135.93, 118.32, 109.44 (thiophene carbons), 39.27, 33.55, 26.86, 26.24 and 13.73 (aliphatic carbons). 2D NMR confirmed that the bromine was bonded to the carbon adjacent to the 3-methyl substituent.

Provenance & Evidence