Dimethylformamide → HCID 118307060, compound

Participants

Reaction Steps

To a mixture of 1-bromo-2-(but-3-en-1-yl)-4-fluorobenzene (0.5 g, 2.183 mmol) in tetrahydrofuran (10 mL) at −78° C. was added BuLi (1.048 mL, 2.62 mmol) dropwise. It was then stirred at this temperature for 1 h, then N,N-dimethylformamide (0.204 mL, 2.62 mmol) was added. The reaction mixture was stirred at −78° C. for 30 min, then warmed up to rt and stirred at rt for 1 h. It was then quenched with NH4Cl, extracted with ether. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by biotage, eluting with 10% EtOAc/hexane to obtain 2-(but-3-en-1-yl)-4-fluorobenzaldehyde (0.35 g, 90%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.22 (s, 1H), 7.88 (dd, J=8.6, 6.1 Hz, 1H), 7.08 (td, J=8.3, 2.6 Hz, 1H), 7.05-6.96 (m, 1H), 6.00-5.73 (m, 1H), 5.12-4.99 (m, 2H), 3.22-3.09 (m, 2H), 2.49-2.34 (m, 2H).

Provenance & Evidence