Bromide ion → HCID 10229033, compound

Participants

Reaction Conditions

Reaction Steps

At 40° C., 5-phenylpentylbromide solution (1.15 g, 5 mmol) in ether (5 mL) was slowly added to magnesium turnings with vigorous agitation under Argon. The exothermic reaction was initialized after addition of one quarter of the bromide solution. Once the addition was completed, the suspension was heated at reflux for 30 minutes and most of magnesium was dissolved. The resulted 1M Grignard reagent was cooled to −70° C. and added the methyl ester (compound 90, 100 mg, 0.25 mmol) in THF solution (2 mL). The mixture was warmed to 25° C. and stirred at that temperature for 20 hours. Saturated amonium chloride (1 mL) was introduced to quench the reaction. The suspension was extracted with ether (1×50 mL). The organic phase was collected, dried and concentrated. The residue was purified by flash column chromatography (25% EtOAc in hexanes) followed by preparative TLC (1% THF in CH2Cl2) to give 1.2 mg (1% yield) of the title compound.

Provenance & Evidence