Réaction #6636

Équation de réaction

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

Compound 71

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

H2SO4

→

title compound

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

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureat reflux for 24 h
3. 3
   ExtractionThe mixture was extracted with hexanes the organic extracts
4. 4
   Lavagewashed successively with water, saturated NaHCO3, water again
5. 5
   Séchagesaturated NaCl and then dried (MgSO4)
6. 6
   AutreThe solvent was removed in vacuo
7. 7
   Autrethe residue purified by flash chromatography (silica; hexanes)

Mode opératoire

A mixture of 500 mg (1.49 mmol) of 4-bromo-2-(1,1,3-trimethyl-3-hydroxybutyl) thiophenol (Compound 71) 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): δ 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 284.0221 (calcd. for C13H17 S Br, 284.0234).

Source