Isobutane → Tert-butyl 4-bromo-3-methylbenzoate

Participants

Reaction Steps

To a solution of the above 4-bromo-3-methylbenzoyl chloride residue in THF (100 mL), a solution of potassium ten-butoxide (6.0 g, 53.5 mmol) in THF (60 mL) was added dropwise at 0° C. under nitrogen. The mixture was stirred at room temperature for 30 min. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over Na2SO4. The compound was purified by silica column chromatography using heptane and ethyl acetate as eluent to give a yield of 96%. 1HNMR (300 MHz, CD2Cl2): δ 7.88 (s, 1H), 7.53-7.7 (m, 2H), 2.42 (s, 3H, CH3), 1.57 (s, 9H, CH3); MS (m/e): calculated 215.96/213.96 (1:1). found 215.0/217.0 (1:1), for [M+H−tBu]+.

Provenance & Evidence