Benzyl Bromide → HCID 11143141, compound

Participants

Reaction Conditions

Reaction Steps

1,3-Dimethoxy-5-bromobenzene (14.5 g, 66.7 mmol) was dissolved in 40 mL CH2Cl2 and cooled to 0° C. BBr3 (100 mL, 1.0 M in CH2Cl2, 100 mmol) was added and the solution was stirred for 12 h at room temperature. The reaction was carefully quenched with MeOH and then concentrated to dryness. The resulting syrup was redissolved in EtOAc and was washed with H2O (3×25 mL). The organic phase was then dried over Na2SO4, filtered and concentrated to dryness. The residue was then dissolved in DMF (50 mL) and K2CO3 (20.2 g, 146.7 mmol) was added, followed by benzyl bromide (BnBr, 17.4 mL, 146.7 mmol). The reaction mixture was stirred for 3 h after which TLC analysis (60% EtOAc/hexanes) indicated that the reaction was complete. The reaction mixture was then diluted in EtOAc and washed with water (3×50 mL). The organic phase was dried over Na2SO4, filtered and concentrated to yield the crude product. The product was crystallized from isopropanol to yield 1,3-bis-Benzyloxy-5-bromobenzene 22 (21 g, 57 mmol, 85° A) yield) as a white powder. 1H NMR (CD2Cl2) δ 7.3-7.5 (m, 10H), 6.71 (s, 2H), 6.60 (s, 1H), 5.05 (s, 4H); 13C NMR (CD2Cl2) δ 161.2, 137.2, 128.9, 128.4, 127.8, 123.1, 111.0, 101.5, 70.0.

Provenance & Evidence