Benzyl Bromide → HCID 10637344, compound

Participants

Reaction Steps

2-Chloro-3,4-dimethyl-6-nitrophenol (6.44 g, 31.9 mmol) was dissolved in dry DMF (105 mL) and flushed with argon. Benzyl bromide (4.17 mL, 35.1 mmol) and K2CO3 (13.24 g, 95.7 mmol) were added. The reaction mixture was stirred at room temperature for 8 h (protected from light) and filtered. Water (5 mL) was added and the solvent was co-evaporated with xylene (2×150 mL) and CH2Cl2 (100 mL). The residue was mixed with CHCl3 (100 mL), filtered and after evaporation of the solvent 10.8 g of crude product remained. Purification by flash column chromatography (SiO2, CHCl3 -Hexane 1:1) gave the title compound (8.44 g). Mp: 74°-75° C.; 1H NMR (DMSO-d6): δ 7.80 (s, 1H), 7.48-7.37 (m, 5H), 5.06 (s, 2H), 2.37 (s, 3H), 2.34 (s, 3H); 13C NMR (DMSO-d6): δ 145.24, 142.22, 142.08, 135.73, 134.73, 129.61, 128.39, 128.37, 128.35, 123.64, 75.74, 19.74, 17.13; MS (EI, 70 eV): m/z (rel.int.) 293/291 (M+, 0.08/0.37), 187/185 (8/24), 91 (100).

Provenance & Evidence