Reaction #1470

Reaction equation

4,4-dimethyl-7-bromo-3,4-dihydronaphthalen-1(2H)one

7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one

Compound G

7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one

THF

thiophenol

triethylamine

THF

→

title compound

4.4-Dimethyl-7-bromo-1-phenylthio-3,4-dihydronaphthalene

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted with ether (3×50 mL)
2. 2
   WashThe combined organic layer was washed successively with water (10 mL), 10% NaHCO3 (10 mL) and brine (10 mL)
3. 3
   DryingThe organic layer was dried (MgSO4)
4. 4
   workup.DISTILLATIONthe solvent distilled off at reduced pressure

Procedure

To a stirred solution of 4,4-dimethyl-7-bromo-3,4-dihydronaphthalen-1(2H)one (Compound G, 1.48 g, 5.9 mmol), titanium tetrachloride (1.09 g, 5.7 mmol) and THF (10 mL) was added a mixture of thiophenol (660 mg, 6 mmol), triethylamine (1.16 g, 11.5 mmol) and THF (20 mL) via an addition funnel at ambient temperature. The mixture was stirred for 5 h, and water (10 mL) was added, extracted with ether (3×50 mL). The combined organic layer was washed successively with water (10 mL), 10% NaHCO3 (10 mL) and brine (10 mL). The organic layer was dried (MgSO4) and the solvent distilled off at reduced pressure. After silicagel chromatography the title compound was obtained as a colorless oil.

Source