Hydrogen Bromide → 5-Nitro-2-phenoxyphenol

Participants

Reaction Conditions

Reaction Steps

3-methoxy-4-phenoxynitrobenzene(2 g, 8.15 mmol) was treated with 48% HBr (20 ml) and HOAc (20 ml), The reaction mixture was heated to 110 ° C. for 24 hours and then the reaction mixture was poured into ice and extracted with EtOAc, the organic layer was washed with brine, dried over Na2SO4. Removal of the solvent provided a brownish residue 5-Nitro-2-phenoxy-phenol which was taken to next step without further purification. (almost quantitative yield). 1H NMR (CDCl3): δ 7.91 (d,1H, 2.7 Hz), 7.72 (dd, 1H, J1=8.8 Hz, J2=2.4 Hz), 7.43 (t, 2H, J=7.9 Hz), 7.28 (d, 1H, 7.9 Hz), 7.10 (d, 1H, J=8.3 Hz), 6.78 (d, 2H, J=8.9 Hz).

Provenance & Evidence