Sodium hydride → 1-(But-3-enyloxy)-4-chloro-2-nitrobenzene

Participants

Reaction Steps

To a solution of 3-butene-ol (1.08 mL, 12.53 mmol) in THF (30 mL) at 0° C. was added NaH (60%, 592 mg, 14.81 mmol). The mixture was stirred for 30 minutes, and 4-chloro-1-fluoro-2-nitrobenzene (2 g, 11.39 mmol) in THF (5 mL) was added dropwise. The reaction mixture was further stirred at 0° C. for 2 hours, poured into ice-water and extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated to give the desired product (2.5 g, 97%). MS (DCI/NH3) m/z: 244.95 (M+H)+; 1H NMR (400 MHz, DMSO-D6) δ ppm 2.47 (q, J=6.55 Hz, 2 H) 4.22 (t, J=6.60 Hz, 2 H) 5.08 (d, J=10.13 Hz, 1 H) 5.15 (dd, J=17.18, 1.84 Hz, 1 H) 5.80–5.91 (m, 1 H) 7.42 (d, J=9.21 Hz, 1 H) 7.70 (dd, J=9.21, 2.76 Hz, 1 H) 8.00 (d, J=2.76 Hz, 1 H)

Provenance & Evidence