2,4-Dichloronitrobenzene → HCID 66821097, compound

Participants

Reaction Conditions

Reaction Steps

4-cyanophenol 4.5 g (23.0 mmol), dissolved in 5 ml of DMF, was added to a stirred suspension of sodium hydride 0.92 g (23.0 mmol) in 5 ml of DMF cooled to 5° C. The reaction flask was stirred for 10 min at the same temperature and this was followed by dropwise addition (over 15 min) of 2,4-dichloronitrobenzene 2.0 g (10.5 mmol) dissolved in 5 ml of DMF. The reaction mixture was stirred for 6 h at 70° C. The reaction mass was poured into ice-cold water and extracted with 200 ml of ethylacetate. The organic phase was washed with 1 M Na2CO3 and saturated brine solution. The solution was dried over sodium sulphate and concentrated to afford an oily residue, which was purified by column chromatography using chlorofrom-ethyl acetate (10:2) to afford 2.5 g of the required product. 1H NMR (DMSO-d6): δ 6.79 (1H, d), 6.93 (1H, d), 7.06 (2H, d), 7.18 (2H, d), 7.75 (4H, d), 8.16 (1H, d).

Provenance & Evidence