Benzene, 1-bromo-3-nitro- → 2-Bromo-6-nitroaniline

HRID 7092

Reaction equation

HRID 7092 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.CO[NH3+:13].[Cl-].CC(C)([O-])C.[K+]>CN(C=O)C.[Cu]Cl>[NH2:13][C:3]1[C:2]([Br:1])=[CH:7][CH:6]=[CH:5][C:4]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 11457Benzene, 1-bromo-3-nitro-HCID 11639O-methylhydroxylammonium chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 114699892-Bromo-6-nitroanilineYield 6%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromonitrobenzene (6.06 g, 30 mmol) and o-methylhydroxylamine hydrochloride (3.13 g, 37.5 mmol) were reacted in the presence of copper (I) chloride (0.59 g, 6 mmol) and potassium t-butoxide (10.1 g, 90 mmol) in DMF (75 mL). Aqueous work-up and chromatography gave 2-amino-3-bromonitrobenzene (0.36 g, 6%) as an orange powder. 1H NMR (CDCl3) δ 6.60 (t, 1H, J=9 Hz), 7.70 (d, 1H, J=9 Hz), 8.14 (d, 1H, J=9 Hz).

Sources & evidence

ORD record
ord-5da6dc30a40e4b98a9086a0a634513ee
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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