Isobutylene → 1-Bromo-3-t-butylthiobenzene

Participants

Reaction Steps

Isobutylene was bubbled through 75% H2SO4 solution at-5 degrees C. until 2.65 g (47.2 mmol) of isobutylene had been absorbed. The mixture was treated with 3.8 g (20.1 mmol) of 3-bromothiophenol and then allowed to warm to room temperature and stirred for 72 hours. The reaction mixture was then poured into 40 ml of an ice/water mixture and then extracted with ether. The ether extracts were combined and washed successively with 5% NaOH, water and saturated NaCl solution and then dried (MGSO4) The solvent was removed in-vacuo and the residue distilled (69-75 degrees C., 0.6 mm) to give the title compound as a pale yellow oil. PMR (CDCl3) & 1.30 (9H, s), 7.23 (1H, t, J~8.0 Hz), 7.45-7.54 (2H, m), 7.72 (1H, t, J~1.8 Hz). 4-Bromophenyl 3-methyl-2-butenyl sulfide (Compound 46)

Provenance & Evidence