تفاعل #6636

معادلة التفاعل

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

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةat reflux for 24 h
3. 3
   استخلاصThe mixture was extracted with hexanes the organic extracts
4. 4
   غسيلwashed successively with water, saturated NaHCO3, water again
5. 5
   تجفيفsaturated NaCl and then dried (MgSO4)
6. 6
   أخرىThe solvent was removed in vacuo
7. 7
   أخرىthe residue purified by flash chromatography (silica; hexanes)

الإجراء التجريبي

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).

المصدر