Allyl bromide → 1-(Allyloxy)-2-chloro-5-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-chloro-5-nitrophenol (13.0 g, 75.1 mmol) in DMF (150 mL) was added K2CO3 (15.5 g, 113 mmol). The mixture was cooled to 0° C., and allyl bromide (9.60 mL, 113 mmol) was added dropwise. The reaction was then allowed to stir overnight at rt under nitrogen. The reaction was concentrated to remove DMF, then EtOAc was added to the residue. The mixture was washed with water and brine. The organic layer was dried (Na2SO4), and concentrated in vacuo to afford the highly yellow solid 2-(allyloxy)-1-chloro-4-nitrobenzene (11.5 g, 72% yield). LC-MS (M+H)+212.2. 1H NMR (400 MHz, CDCl3) δ ppm 7.81-7.77 (2H, m), 7.52 (1H, d, J=8.8 Hz), 6.12-6.02 (1H, m), 5.54-5.37 (2H, m), 4.72-4.70 (2H, m).

Provenance & Evidence