Acetic Acid → Benzenamine, 3-bromo-4-methyl-
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH3:11].C(O)C.C(O)(=O)C.N>O.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH3:11]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
30 g (139 mmol) of 2-bromo-4-nitrotoluene are placed in 180 ml of water, 400 ml of ethanol and 110 ml of acetic acid in a round-bottomed flask and under a stream of nitrogen. The medium is heated to 70° C. and 31 g (556 mmol) of iron are added portionwise. The mixture is refluxed for 2 hours and, after cooling, 180 ml of 34% aqueous ammonia are added slowly. The mixture is filtered through Celite and the organic phase is extracted with water and ethyl acetate. It is then dried over magnesium sulfate, filtered and then evaporated. 25.5 g (100%) of the expected product are obtained in the form of a brown oil.
Workup
- temperatureThe mixture is refluxed for 2 hours
- temperatureafter cooling
- filtrationThe mixture is filtered through Celite
- extractionthe organic phase is extracted with water and ethyl acetate
- dry with materialIt is then dried over magnesium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-e312b2f9061442c5b2573add0e031ecb
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06924400B2
Reaction notes
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