Bromine → N-(4-bromo-3-methylphenyl)-2-methylbenzamide
Reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)=[O:5].[Br:18]Br>C(O)(=O)C>[Br:18][C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=2[CH3:1])=[CH:8][C:9]=1[CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 12.5 °C
Procedure
3-(2-methylbenzoylamino)toluene (80 g) is dissolved in acetic acid (500 mL), and thereto is added a solution of bromine (19.0 ml) in acetic acid (40 mL) with stirring under ice cooling over a period of about one hour. During which the mixture is cooled at an inner temperature of below 20° C. (mean inner temperature: 10-15° C.) since the temperature raises. The reaction mixture is continuously stirred overnight. The resulting suspension is added to ice-water, and the resulting crystals are taken by filtration, washed with water, and dried at 60° C. The resultant is recrystallized from methanol-water to give 2-bromo-5-(2-methylbenzoylamino)toluene (105.0 g), white needles (yield 97%, Mp 144.5-146.0° C.)
Workup
- temperatureraises
- waitThe reaction mixture is continuously stirred overnight
- filtrationthe resulting crystals are taken by filtration
- washwashed with water
- customdried at 60° C
- customThe resultant is recrystallized from methanol-water
Sources & evidence
- ORD record
- ord-a2992c7e8d9042fda80efe74c5f991e8
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273735B2
Reaction notes
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