Allyl Alcohol → HCID 21075356, compound

Participants

Reaction Steps

To a mixture of anhydrous THF (200 mL) and 95% NaH (757 mg, 29.96 mmol) at 0° C. under N2 was added allyl alcohol (2.04 mL, 29.96 mmol) dropwise. After 0.5 hour, 4-bromo-1-fluoro-2-nitro-benzene (5.07 g, 23.04 mmol) was added dropwise. The reaction was warmed from 0° C. to room temperature under N2 overnight, and inorganic salt was filtered. The filtrate was concentrated with silica gel powder (20 g), and purified by flash chromatogrphy eluting with 10% ethyl acetate in hexanes (1 L) and 20% ethyl acetate in hexanes (1 L) to give the title compound (5.06 g, 85%). MS (DCI) m/z 257.35 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 4.65–4.70 (m, 2 H) 5.35 (m, 1 H) 5.48 (m, 1 H) 6.02 (m, 1 H) 6.97 (d, J=9.16 Hz, 1 H) 7.61 (dd, J=8.99, 2.54 Hz, 1 H) 7.97 (d, J=2.37 Hz, 1 H).

Provenance & Evidence