Reacción #80652

Ecuación de reacción

4-bromo-2-(1,1,3-trimethyl-3-hydroxybutyl) thiophenol

Compound 32

4-bromo-2-(1,1,3-trimethyl-3-hydroxybutyl) thiophenol

H2SO4

→

title compound

2,2,4,4-Tetramethyl-6-bromothiochroman

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaat reflux for 24 h
3. 3
   ExtracciónThe mixture was extracted with hexanes
4. 4
   Lavadowashed successively with water, saturated NaHCO3, water again
5. 5
   Secadosaturated NaCl and then dried (MgSO4)
6. 6
   OtroThe solvent was removed in vacuo
7. 7
   Otrothe residue purified by flash chromatography (silica; hexanes)

Procedimiento

A mixture of 500 mg (1.49 mmol) of 4-bromo-2-(1,1,3-trimethyl-3-hydroxybutyl) thiophenol (Compound 32) and 8 ml of 20 percent aqueous H2SO4 was heated at reflux for 24 h. The mixture was extracted with hexanes, the organic extracts were combined and washed successively with water, saturated NaHCO3, water again, saturated NaCl and then dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash chromatography (silica; hexanes) to give the title compound as a colorless oil. PMR (CDCl3): & 1.35 (6H, s), 1.40 (6H, s), 1.93 (2H, s), 7.17 (1H, dd, J-8.4 Hz, 2.1 Hz), 7.23 (1H, d, J-8.4 Hz), 7.26 (1H, d, J-2.1 Hz). MS exact mass, m/e 16 284.0221 (calcd. for C13H17S Br, 284.0234).

Fuente