Benzoyl Peroxide → HCID 58567061, compound

Participants

Reaction Steps

N-bromosuccinimide (1.95 g, 10.99 mmol), 6-methylpicolinic acid tert-butyl ester (2.1175 g, 10.96 mmol), and benzoyl peroxide (0.27 g, 1.10 mmol, 0.1 eq.) were dissolved in CCl4 (150 mL) and refluxed for 6.5 hours while monitored by TLC (3:1 hexane: ethyl acetate, Rf=0.28). The reaction mixture was filtered and the solvent was removed in vacuo. The light orange oil was redissolved in DCM and extracted three times with an aqueous solution of saturated NaHCO3 (50 mL). The organic layer was dried with MgSO4 and the solvent was removed in vacuo. The crude product was recrystallised twice from a hexane/ethyl acetate mixture (3:1) in the freezer afford the mono-brominated product as small off-white crystals (0.511 g, 1.88 mmol, 17.1%). 1H NMR (300 MHz, CDCl3, δ): 7.92 (d, 1H, ortho-H), 7.82 (t, 1H, meta-H), 7.65 (d, 1H, ortho-H), 4.65 (s, 2H, CH2), 1.64 (s, 9H, tBu-CH3). 13C NMR (300 MHz, CDCl3, δ): 171.0, 161.0, 157.9, 138.4, 127.0, 124.4, 60.9, 33.9, 28.6.

Provenance & Evidence