Benzoyl Peroxide → 4,6-Dibromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

반응식

C1C2C(=CC=CC=2)C=CC=1.[Br:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([CH3:23])([CH3:22])[CH2:17][CH2:16][CH2:15]2.[Br:24]C1C=CC2C(=CC=CC=2)C=1Br.BrN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[Br:24][CH:15]1[C:14]2[C:19](=[CH:20][CH:21]=[C:12]([Br:11])[CH:13]=2)[C:18]([CH3:23])([CH3:22])[CH2:17][CH2:16]1

참가 물질

반응물 4

HCID 7187Benzoyl Peroxide

HCID 67184N-bromobutanimide

HCID 2262911,2-Dibromonaphthalene

HCID 196949766-Bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene naphthalene3회

생성물 1

HCID 196949614,6-Dibromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

실험 절차

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.