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

HRID 543147Notes

Reaction equation

HRID 543147 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 8471Triethylamine2×HCID 124712,4,6-TrichloroanilineHCID 61147Bromoacetyl bromide

Product 1

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

Conditions

Temperature
0 °C

Procedure

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

Workup

  1. additionwas added
  2. temperatureto warm to room temperature
  3. washthe solvent was washed with saturated sodium bicarbonate solution
  4. customThe methylene chloride layer was separated
  5. customprecipitated from solution
  6. filtrationThe solid was filtered
  7. customair dried

Sources & evidence

ORD record
ord-0aa3ce29adb84aac907bda7a6cd13531
Source dataset
uspto-grants-1987_04
Patent number
US04661494

Reaction notes

Loading…