Reaction #1316

Reaction equation

Compound F

6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene naphthalene

benzoylperoxide

6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene naphthalene

Compound F

6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene naphthalene

N-bromosuccinimide

dibromonaphthalene

→

Compound I

4,6-dibromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

Conditions

Procedure

Employing the above-described procedure for the conversion of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene naphthalene (Compound F) to the dibromonaphthalene derivative (Compond I), 3.5 g (14.6 mmol) of (Compound F), 2.86 g (16.1 mmol) of N-bromosuccinimide and 150 mg (0.62 mmol ) of benzoylperoxide gave crude 4,6-dibromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene (Compound I). To a solution of this crude dibromonaphthalene derivative (Compound I) in 50 ml of THF was added 5.38 g (47.1 mmol) of potassium thioacetate. The mixture was refluxed for 6 hours under argon atmosphere, filtered through celite and concentrated in vacuo. Purification by chromatography (silica, 10% EtOAc-hexane) yielded the title compound as red oil.

Source