1-Bromo-3-methylbutane → HCID 78878307, compound

Participants

Reaction Steps

Methyl-4-hydroxyphenylacetate (2.00 g, 12.0 mmol) was added in one portion to a stirred suspension of sodium hydride (60% mineral oil suspension; 528 mg, 13.2 mmol) in dimethylformamide (20 mL) at room temperature under nitrogen. After stirring for 30 min 1-bromo-3-methylbutane (1.99 g, 1.58 mL, 13.2 mmol) was added dropwise over 5 min then stirring was continued for 12 h. The volatiles were evaporated then the residue partitioned between dichloromethane (50 mL) and water (50 mL). The phases were separated and the aqueous phase was washed with dichloromethane (2×50 mL). The organics were combined, dried (magnesium sulfate) and the solvent evaporated. The residue was chromatographed on silica gel (20% diethyl ether: cyclohexane) to give the title compound as a colourless oil (2.16 g, 76%). LC/MS: 3.51 min; z/e 254, calcd (M+18) 254. 1H NMR (400 MHz: CDCl3): 7.15 (2H), 6.85 (2H), 4.00 (2H), 3.70 (3H), 3.55 (2H), 1.85 (1H), 1.70 (2H), 0.95 (6H).

Provenance & Evidence