1-Pentene, 5-bromo- → 5-Methyl-2-(pent-4-enyl)benzaldehyde

Participants

Reaction Steps

Step AI (4): 1-Bromo-2-(dimethoxymethyl)-4-methylbenzene (615 mg, 2.51 mmol) was dissolved in THF (10 mL) under N2 atmosphere at −78° C. n-Butyllithium (1.6 M, 3.1 mL) was added and the reaction mixture was stirred for 30 min. 5-Bromopent-1-ene (0.31 mL, 2.64 mmol) was added. The reaction mixture was warmed to rt and stirred for 18 h. The reaction was quenched with the addition of HCl (1.0 N) and was further stirred at rt for 1 h. The reaction mixture was extracted with EtOAc and washed with brine. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography to give 5-methyl-2-(pent-4-enyl)benzaldehyde (45 mg, 10%) as a colorless oil. LC-MS (M+H)+=189.41.

Provenance & Evidence