4-Bromothiophenol → S-(4-bromophenyl) 3,3-dimethylthioacrylate

Participants

Reaction Conditions

Reaction Steps

To an ice bath cooled solution of 1.92 g (80 mmol) of NaH (obtained from a 60% suspension in mineral oil by 3×15 ml hexane wash) in 30 ml of dry THF was added slowly under argon a solution of 15.1 g (80 mmol) of 4-bromothiophenol in 60 ml of dry THF over 1 h. The mixture was stirred at 0 degrees C. for a further 30 min and then treated with a solution of 10.1 g (85 mmol) of dimethylacryloyl chloride in 30 ml of dry THF. The cooling bath was then removed and the mixture then stirred at room temperature for 40 h. The reaction mixture was poured into 200 ml of water containing 2 ml of glacial acetic acid and the organic layer was separated. The organic layer was washed with 2×75 ml of water and then dried (MgSO4). The solvent was removed in vacuo to give the title compound as a yellow oil. PMR (CDCl3): & 1.91 (3 H, s), 2.14 (3 H, s), 6.03-6.06 (1 H, m), 7.28 (2 H, d, J~8.6 Hz), 7.53 (2 H, d, J~8.6 Hz).

Provenance & Evidence