2-Bromobenzoic acid → 2-bromo-N-(4-nitrophenyl)benzamide

HRID 5676

Reaction equation

S(Cl)(Cl)=O.[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O.[N+:15]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)([O-:17])=[O:16]>C1(C)C=CC=CC=1.CN(C)C=O.CN1C(=O)CCC1>[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH:22][C:21]1[CH:23]=[CH:24][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=1)=[O:10]

Participants

Conditions

Temperature: 80 °C

Procedure

Thionyl chloride (120.5 g) was added to a stirred mixture of 2-bromobenzoic acid (194 g) in toluene (500 ml) and N,N-dimethylformamide (DMF) (5 ml) and the mixture heated at 80° C. for 4 hours. The solution was cooled to 20° C. and added slowly to a solution of 4-nitroaniline (133.1 g) in toluene (500 ml) and NMP (120 ml), maintaining the temperature of the reaction mixture between 20°-25° C. The reaction mixture was then stirred for 24 hours when a solid precipitated. Water (360 ml) was added with rigorous stirring and the suspended solid collected by filtration, and washed successively with water, toluene and acetonitrile to give 2-bromo-N-(4-nitrophenyl)benzamide as a solid, in 87% yield, which was used without further purification or characterisation.

Workup

temperatureThe solution was cooled to 20° C.
temperaturemaintaining the temperature of the reaction mixture between 20°-25° C
customprecipitated
additionWater (360 ml) was added
stirringwith rigorous stirring
filtrationthe suspended solid collected by filtration
washwashed successively with water, toluene and acetonitrile

Sources & evidence

ORD record: ord-55c8dbdb7e544eb9a79fb8565a5af017
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05245035

Linked notes

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