Methanol → 2-Methoxy-2'-nitro-4,4'-dibromobiphenyl

HRID 79852

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[N+:15]([O-:17])=[O:16])=[C:4]([N+]([O-])=O)[CH:3]=1.[CH3:21][O-:22].[Na+].CO>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[N+:15]([O-:17])=[O:16])=[C:4]([O:22][CH3:21])[CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To the solution of 4,4′-dibromo-2,2′-dinitro-biphenyl (6.58 g, 16.5 mmol) in DMF (50 ml) at 0° C. was added a solution of sodium methoxide in Methanol (4.4 M, 4.5 ml, 19.8 mmol). The mixture was stirred at 25° C. for 12 hours and was poured into ice-water (140 ml). The mixture was extracted with EtOAc (2×). The combined organic phase was washed with water and brine and dried with Na2SO4. Concentration under reduced pressure gave pale solid. The re-crystallization from CH3CN/MeOH gave 4,4′-dibromo-2-methoxy-2′-nitro-biphenyl as a white solid (3.76 g).

Workup

extractionThe mixture was extracted with EtOAc (2×)
washThe combined organic phase was washed with water and brine
dry with materialdried with Na2SO4
concentrationConcentration under reduced pressure
customgave pale solid
customThe re-crystallization from CH3CN/MeOH

Sources & evidence

ORD record: ord-a82ef3c06d9e4a16872ba8ff2dba8161
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841278B2

Linked notes

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