Sodium Hydroxide → 1-Bromo-4-(3-methylbut-2-enylsulphanyl)benzene

A mixture of 12.8 g (67.7 mmol) of 4-bromothiophenol (Compound 40) and 2.7 g (67.7 mmol) of sodium hydroxide in 50 ml acetone was heated at reflux under argon for 2.5 hours. The refluxing mixture was then treated dropwise with a solution of 10.0 g (67.1 mmol) of 4-bromo-2-methyl-2-butene (Compound 45) in 10 ml acetone and the mixture heated at reflux for a further 24 hours. The mixture was then cooled and solvent removed in-vacuo. The residue was treated with 50 ml water and extracted with 3×75 ml ether. The ether extracts were combined and washed successively with 3×30 ml of 5% NaOH, 50 ml of water and 50 ml of saturated NaCl and then dried (MgSO4). Solvent was then removed in-vacuo and the residual oil purified by kugelrohr distillation (70 degrees C., 0.1 mm) to give the title compound as a colourless oil. PMR (CDCl3 ): & 1.58 (3H, s), 1.70 (3H, s) 3.5 (2H, d, J~7.0 Hz), 5.27 (1H, t, J~7.0 Hz), 7.17 (2H, d, J~8.3 Hz), 7.36 (2H, d, J~8.3 Hz).

1. temperaturewas heated
2. temperatureat reflux under argon for 2.5 hours
3. temperaturethe mixture heated
4. temperatureat reflux for a further 24 hours
5. temperatureThe mixture was then cooled
6. customsolvent removed in-vacuo
7. additionThe residue was treated with 50 ml water
8. extractionextracted with 3×75 ml ether
9. washwashed successively with 3×30 ml of 5% NaOH, 50 ml of water and 50 ml of saturated NaCl
10. dry with materialdried (MgSO4)
11. customSolvent was then removed in-vacuo
12. distillationthe residual oil purified by kugelrohr distillation (70 degrees C., 0.1 mm)

ORD record

ord-b9593a62c4a34db8bff9a2950104566c

Source dataset

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05414007