Reaction #1471

Reaction equation

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

Compound G

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

ethanethiol

triethylamine

→

title compound

2-Bromo-5,6-dihydro-5,5-dimethyl-8-(ethylthio)-naphthalene

Solvents

water

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction stirred at room temperature for 13 h
2. 2
   Extractionextracted with ether (2×)
3. 3
   WashThe organic phase was washed with brine
4. 4
   Dryingdried over Na2SO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherPurification by flash chromatography (silica, 100% hexane)

Procedure

To a solution of 1.03 g (4.1 mmol) of 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G) in 30.0 mL of tetrahydrofuran, was added dropwise 0.49 g (0.85 mL, 7.8 mmol) of titaniumtetrachloride and the resulting solution stirred for 10 min. A solution of 35 mg (0.50 mL, 6.7 mmol) of ethanethiol and 0.54 g (0.75 mL, 5.4 mmol) of triethylamine in 10.0 mL of tetrahydrofuran was added and the reaction stirred at room temperature for 13 h. The mixture was diluted with water and extracted with ether (2×). The organic phase was washed with brine, dried over Na2SO4 and then concentrated in vacuo. Purification by flash chromatography (silica, 100% hexane) gave the title compound as an off.

Source