Azobisisobutyronitrile → Methyl 2-(bromomethyl)-3-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-methyl-3-nitrobenzoate (5 g, 25.6 mmol) in dry DCM (20 mL) were added NBS (4.56 g, 25.6 mmol) and AIBN (0.421 g, 2.56 mmol) and the mixture was stirred at 60° C. After 20 h, additional AIBN (0.42 g) was added and the mixture continued to be stirred at 60° C. After 72 h, the mixture was filtered and concentrated. Purification by flash chromatography (100% hexanes to 10% EtOAC/hexanes) afforded 18 (5.2 g, 74%) as a light yellow solid. Rf=0.3 (9:1 hexanes:ethyl acetate). 1H NMR (400 MHz, CDCl3) δ 8.11 (dd, J=7.9, 1.4 Hz, 1H), 8.03-7.91 (m, 1H), 7.54 (dd, J=8.0 Hz, 8.0 Hz, 1H), 5.24-5.03 (s, 2H), 4.08-3.88 (s, 3H). MS (ESI) m/z calcd for C9H9BrNO4 [M+H]+ 275.1, found 275.5.

Provenance & Evidence