Hexane → Methyl 3-bromo-4-methylbenzoate

Participants

Reaction Steps

To a mixture of hexane washed 60% disp. NaH (2.28 g, 57 mmol) in DMF (250 mL), 0° C., was added 3-bromo-4-methylbenzoic acid (10.03 g, 46.6 mmol). After 30 min, the reaction was warmed to room temperature, diluted with EtOAc (1.25 L) and washed with H2O (5×250 mL). The organic layer was MgSO4 dried and concentrated. The residue was chromatographed (˜375 g silica, 10% EtOAc/CH2Cl2) to give the desired product as a solid (16.68 g, 63%); IR(CHCl3): 1260, 1294, 1437, 1721 cm−1; NMR(300 MHz, CDCl3): 2.46 (s, 3H); 3.92 (s, 3H); 7.31 (d, 1H, J=7.8 Hz); 7.88 (d, 1H, J=7.8 Hz); 8.21 (s, 1H); MS(FD): 228.0.

Provenance & Evidence