Triethylamine → 2-bromo-N-(4-bromo-2,6-dimethylphenyl)propionamide

HRID 2079566Notes

Reaction equation

HRID 2079566 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.C(N(CC)CC)C.[Br:18][CH:19]([CH3:23])[C:20](Br)=[O:21].C(=O)([O-])O.[Na+]>O1CCCC1>[Br:18][CH:19]([CH3:23])[C:20]([NH:6][C:5]1[C:7]([CH3:9])=[CH:8][C:2]([Br:1])=[CH:3][C:4]=1[CH3:10])=[O:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 905494-Bromo-2,6-xylidineHCID 516892Sodium Bicarbonate

Product 1

HCID 600353552-bromo-N-(4-bromo-2,6-dimethylphenyl)propionamideYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2,6-dimethylaniline (100.0 g) in tetrahydrofuran (400 mL) was added triethylamine (60.7 g) and 2-bromopropionyl bromide (129.5 g) under ice-cooling. The mixture was stirred at room temperature for 1 hour and cooled in an ice-cooling bath. To the reaction mixture was added a sodium hydrogencarbonate aqueous solution and the mixture was stirred at room temperature for 30 minutes. The precipitate was collected by filtration, washed with water and diethyl ether, and dried to give 2-bromo-N-(4-bromo-2,6-dimethylphenyl)propionamide (151.2 g).

Workup

  1. temperaturecooling
  2. temperaturecooling bath
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-650d98d4051b4cfeb5a35e9b1dadb9c2
Source dataset
uspto-grants-2011_04
Patent number
US07932259B2

Reaction notes

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