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

HRID 1220

Reaktionsgleichung

Reaktionsgleichung von HRID 1220
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

Komponenten

5

Edukt 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2262911,2-DibromonaphthaleneHCID 196949766-Bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene naphthalene3×

Produkt 1

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

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-0a6411cd1b2143cf95c4b57b2c8fb6d3
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723620

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