Dimethylformamide → 4-(Trimethylsilyl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

1-Bromo-4-(trimethylsilyl)benzene (1.15 g, 5 mmol) was dissolved in THF (30 ml) and cooled to −78° C. Under argon a 1.6 M solution of n-butyl lithium in hexane (3.13 ml, 5 mmol) was added dropwise keeping the temperature below −70° C. The clear colorless solution was stirred at −78° C. for 15 min and DMF (1.16 ml, 15 mmol) was added quickly. The reaction temperature raised to −68° C. The reaction was stirred for additional 15 min at −78° C., quenched with 1N aq. HCl solution and extracted twice with diethyl ether. The combined organic layers were washed twice with water and once with sat. aq. NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to yield 4-trimethylsilanyl-benzaldehyde (920 mg, 100%) as a colorless oil. The product was pure enough to be used directly in the next step. MS (ISP): 179.2 (M+H)+. 1HNMR (CDCl3, 300 MHz): δ 10.02 (s, 1H) 7.84 (d, 2H), 7.69 (d, 2H), 0.31 (s, 9H).

Provenance & Evidence