2-Nitrobiphenyl → 4'-Bromo-2-nitrobiphenyl

HRID 628213

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O-:3])=[O:2].[Br:16]Br.S(=O)(=O)(O)[O-].[Na+]>[Fe](Cl)(Cl)Cl.O>[Br:16][C:13]1[CH:12]=[CH:11][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A three neck flask was charged with 2-nitrobiphenyl (1 mol), iron trichloride (55 mmol), and water (200 mL) and set to stir under a nitrogen atmosphere for 30 minutes. Bromine (1.25 mol) was added dropwise over the course of one hour, then set to reflux for four hours, cooled to 60° C., and stirred for 12 hours. Sodium bisulfate (500 mmol) was added slowly, and the mixture rinsed three times with water (200 mL), twice with 5% sodium hydroxide solution (100 ml) and twice more with water (200 mL). The solids were dissolved in dichloromethane, dried over magnesium sulfate, and flashed chromatographed over silica with dichloromethane as the eluent. The solvent was removed under reduced pressure and the crude product recrystallized from ethanol to give 4′-bromo-2-nitrobiphenyl in 35% yield.

Workup

temperatureto reflux for four hours
stirringstirred for 12 hours
washthe mixture rinsed three times with water (200 mL)
dissolutionThe solids were dissolved in dichloromethane
dry with materialdried over magnesium sulfate
customflashed chromatographed over silica with dichloromethane as the eluent
customThe solvent was removed under reduced pressure
customthe crude product recrystallized from ethanol

Sources & evidence

ORD record: ord-c9cc7bbbc0a64954932224745e35b818
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09312502B2

Linked notes

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