1,3-Dibromobenzene → HCID 54317339, compound

HRID 581912Notes

Reaction equation

[C:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)(=[O:3])[CH3:2].[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]>[Br:14][C:15]1[CH:16]=[C:17]([NH:8][C:7]2[CH:9]=[CH:10][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][C:6]=2[N+:11]([O-:13])=[O:12])[CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 4-acetyl-2-nitroaniline (3.41 g, 18.94 mmol), 1,3-dibromobenzene (4.6 ml, 38.06 mmol), potassium carbonate (2.62 g, 19 mmol) and a catalytic amount of copper bronze is heated with stirring to 180° C. under a stream of nitrogen for 2 days. After cooling the solid reaction cake is extracted with a mixture of dichloromethane and methanol (9:1). The extract is concentrated under reduced pressure. The residue is extracted with ethyl acetate. This extract is concentrated under reduced pressure and the residue is eluted through silica gel with a mixture of petroleum ether and ethyl acetate (4:1) to afford the pure product. Yield 0.67 g (10.6%). Mp. 142-144° C.

Workup

temperatureAfter cooling
customthe solid reaction cake
extractionis extracted with a mixture of dichloromethane and methanol (9:1)
concentrationThe extract is concentrated under reduced pressure
extractionThe residue is extracted with ethyl acetate
concentrationThis extract is concentrated under reduced pressure
washthe residue is eluted through silica gel with a mixture of petroleum ether and ethyl acetate (4:1)
customto afford the pure product

Sources & evidence

ORD record: ord-89337d7dbf0042e6a31750e6bbde88a5
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922725

Reaction notes

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