Carbon Dioxide → Benzenamine, 4-bromo-N-methyl-

HRID 1057289Notes

Reaction equation

HRID 1057289 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:9]Br.C(=O)([O-])[O-].[Na+].[Na+].C(=O)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([NH:2][CH3:1])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 7515N-MethylanilineHCID 10340Sodium CarbonateHCID 24408Bromine

Product 1

HCID 2757052Benzenamine, 4-bromo-N-methyl-Yield 141.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

10.7 g N-methylaniline (XXI), 32.1 g tetrabutylammonium bromide [(C4H9)4N+Br31]and 100 ml methylene chloride (CH2Cl2) were placed in a three-necked flask and cooled down to 0° C. with iced saline. 15.8 g bromine (Br2) was dropped slowly with stirring and was stirred for 4 hours while maintaining at 0° C. The temperature was allowed to raise to room temperature and saturated sodium carbonate solution was dropped slowly till evolution of carbon dioxide is ceased. Water layer was separated and extracted with methylene chloride for three times. The organic layers were combined and dried over anhydrous sodium sulfate. Methylene chloride was evaporated to yield 26 g 4-bromo-N-methylaniline (XXII).

Workup

  1. stirringwas stirred for 4 hours
  2. temperaturewhile maintaining at 0° C
  3. temperatureto raise to room temperature
  4. customWater layer was separated
  5. extractionextracted with methylene chloride for three times
  6. dry with materialdried over anhydrous sodium sulfate
  7. customMethylene chloride was evaporated

Sources & evidence

ORD record
ord-ada22a29e0cf4cd2ac711d966c818dea
Source dataset
uspto-grants-2003_02
Patent number
US06514956B1

Reaction notes

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