Bromine → N-(4-Bromo-3-chloro-2-methylphenyl)acetamide

HRID 1157663Notes

Reaction equation

HRID 1157663 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[Br:13]Br>C(O)(=O)C>[Br:13][C:7]1[CH:6]=[CH:5][C:4]([NH:8][C:9](=[O:11])[CH3:10])=[C:3]([CH3:12])[C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 81969N-(3-chloro-2-methylphenyl)acetamide

Product 1

HCID 86376N-(4-Bromo-3-chloro-2-methylphenyl)acetamideYield 93.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve N-(3-chloro-2-methyl-phenyl)-acetamide (120.0 g, 0.653 mol) in acetic acid and cool to 0° C. Add bromine (313.3 g, 1.96 mol) dropwise over 30 min via an addition funnel. Stir for 17 h while allowing the reaction to warm to room temperature. Pour the reaction into 1 L of ice, and filter. Rinse the filter cake with 4 L of water. The title product is isolated in 93.6% yield (160.6 g) as a white solid. MS: MS (ESI−): 262 (M−1)−. MS (ESI+): 263 (M+1)+.

Workup

  1. customthe reaction
  2. temperatureto warm to room temperature
  3. additionPour
  4. filtrationfilter
  5. washRinse the filter cake with 4 L of water

Sources & evidence

ORD record
ord-d9d9c2b6c46f4c54b4b8b8dd8b802dde
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

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