Benzylamine → Benzyl-(3-bromo-5-ethoxymethyl-2-methyl-phenyl)-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,3-dibromo-5-ethoxymethyl-2-methyl-benzene (1.322 g, 4.29 mmol), benzylamine (0.49 mL, 4.507 mmol), Pd2(dba)3 (409 mg, 0.447 mmol), rac-BINAP (811 mg, 1.302 mmol), NaOtBu (618 mg, 6.435 mmol) and toluene (30 mL) was heated at 80° C. for 1 h 45 minutes. The reaction was cooled, poured onto water and extracted with EtOAc (×3). The organics were washed with water, brine and dried (Na2SO4). Chromatography (Hexanes/EtOAc) afforded benzyl-(3-bromo-5-ethoxymethyl-2-methyl-phenyl)-amine (1.268 g) as a yellow liquid. 1H NMR (400 MHz, d6-DMSO) δ: 1.24 (t, 3H), 2.32 (s, 3H), 3.50 (q, 2H), 4.04 (bs, 1H), 4.41 (s, 4H), 6.61 (s, 1H), 7.00 (s, 1H), 7.35 (m, 5H) ppm.

Provenance & Evidence