Dichloromethane → alpha-Bromo-(2,4,6-trichlorophenyl) acetamide

HRID 1982405Notes

Reaction equation

HRID 1982405 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([Cl:10])[C:3]=1N.C(Cl)Cl.[Br:14][CH2:15][C:16](Br)=[O:17].C([N:21](CC)CC)C>>[Br:14][CH:15]([C:3]1[C:2]([Cl:1])=[CH:8][C:7]([Cl:9])=[CH:6][C:5]=1[Cl:10])[C:16]([NH2:21])=[O:17]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 124712,4,6-TrichloroanilineHCID 61147Bromoacetyl bromide

Product 1

HCID 23316556alpha-Bromo-(2,4,6-trichlorophenyl) acetamide

Procedure

2,4,6-trichloroaniline, 49.1 gm, was added to 250 ml of methylene chloride. The solution was cooled to 0° C. to 5° C. After cooling, 34.8 gm of triethylamine was added to the system. Then 21.8 ml of bromoacetyl bromide was added and the system allowed to warm to room temperature. The system was stirred at room temperature for 18 hours. The reaction was then stopped and the methylene chloride solution was washed with saturated sodium bicarbonate solution. The methylene chloride layer was separated and partially stripped when a solid precipitated. The solid was filtered and air dried to yield 41.4 gm of the α-bromo-(2',4',6'-trichlorophenyl)acetamide as a gray solid.

Workup

  1. temperatureThe solution was cooled to 0° C. to 5° C
  2. temperatureAfter cooling
  3. washthe methylene chloride solution was washed with saturated sodium bicarbonate solution
  4. customThe methylene chloride layer was separated
  5. customprecipitated
  6. filtrationThe solid was filtered
  7. customair dried

Sources & evidence

ORD record
ord-50395a036fae4603b65de6826b84c6eb
Source dataset
uspto-grants-1986_06
Patent number
US04596813

Reaction notes

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