1,2-Dibromoethane → Benzene, 2-(2-bromoethoxy)-4-methyl-1-nitro-

Participants

Reaction Conditions

Reaction Steps

122.5 g (800 mmol) 5-methyl-2-nitrophenol, 751.0 g (4000 mmol) 1,2-dibromoethane, 110.7 g (800 mmol) K2CO3 were suspended in 400 ml anhydrous DMF. The suspension was heated at 120° C. for 1 hour, then cooled and most of the liquid was evaporated. The residue was dissolved in 1 l CHCl3 and 1 l water. The organic layer was washed with 2×1 l of 1.8% NaOH till the aqueous layer became pale yellow. The organic layer was dried over Na2SO4 for 18 h, filtered and the solvent was evaporated to give ˜240 g oil. The oil was triturated with 240 ml boiling methanol and allowed to settle for 2 h. The resultant precipitate was filtered, washed with 2×100 ml cold methanol and dried at RT for 18 h to afford 89.4 g (43%) off-white crystal. H1NMR (CDCl3) δ (ppm): 2.40(s, 3H), 3.65(t,2H), 4.30(t,2H), 6.85(d,2H), 7.75(d,1H).

Provenance & Evidence