Sulfuric Acid → 4-Bromo-2-(1,1,3-trimethyl-3-hydroxybutyl) thiophenol

Participants

Reaction Steps

To 3.49 g (32.8 mmol) of lithium perchlorate was added under argon 35 ml of 3.0M (105 mmol) methyl magnesium bromide in ether. The above mixture was treated dropwise with stirring with a solution of 2.961 g (10.926 mmol) of 4,4-dimethyl-6-bromo-2-oxo-thiochroman (Compound 70) and the reaction mixture was then heated at reflux for 70 h. The reaction mixture was then allowed to cool and poured onto a mixture of 100 g of ice and 8 ml of conc. H2SO4. The organic layer was separated and the aqueous layer was extracted with 2×25 ml of ether. The organic layers were combined and washed successively with 2×25 ml of saturated NaHCO3 solution, 25 ml of water and 25 ml of saturated NaCl solution and then dried (MgSO4). The solvent was removed in-vacuo and the residue purified by flash chromatography to give the title compound as pale yellow oil. PMR (CDCl3): δ 1.05 (6H, s), 1.52 (6H, s), 2.30 (2H, s), 3.71 (1H, s), 7.22 (1H, dd, J~8.5 Hz, 2.1 Hz), 7.28 (1H, d, J~8.5 Hz), 7.35 (1H, d, J~2 1 Hz)

Provenance & Evidence