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

Temperature

0 °C

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).

1. washwash) in 30 ml of dry THF
2. customThe cooling bath was then removed
3. stirringthe mixture then stirred at room temperature for 40 h
4. additionThe reaction mixture was poured into 200 ml of water containing 2 ml of glacial acetic acid
5. customthe organic layer was separated
6. washThe organic layer was washed with 2×75 ml of water
7. dry with materialdried (MgSO4)
8. customThe solvent was removed in vacuo

ORD record

ord-d1f92dc70dd5417fad441d32e055d30e

Source dataset

uspto-grants-1994_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05278318