Benzene, 1-bromo-3,5-dimethyl- → HCID 18392763, compound

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Reaction Steps

1.42 g (4.50 mmol) of (N-Methoxy-N-methyl)-(4-(S)-(3,4-dichlorophenyl)-6-heptenyl)-amide (prepared in Example 134) was dissolved in 20 mL of dry THF. To it added 10 mL THF solution of 3,5-dimethylphenylmagnesium bromide prepared from 1.8 g (9.6 mmol) of 5-bromo-m-xylene and 463 mg of magnesium turnings. After stirring for 2 hr at rt, the reaction was quenched with saturated aqueous ammonium chloride solution. THF was removed under reduced pressure. The residual material was diluted with ethyl acetate. The organic phase was separated, aqueous phase was extracted twice with ethyl acetate. Combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, filtered, concentrated, chromatographed on silica gel eluting with a gradient of hexane ethyl acetate=10:1 to 5:1 to give 1.57 g of 4-(S)-(3,4-dichlorophenyl)-1-(3,5-dimethylphenyl)-hept-6-ene-1-one (97%).

Provenance & Evidence