Triethylamine → 4-bromo-N-(4-bromo-2-fluorobenzyl)-2-nitrobenzamide

HRID 1639297

Reaction equation

HRID 1639297 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([F:10])[CH:3]=1.C(N(CC)CC)C.[Br:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[C:21]([N+:28]([O-:30])=[O:29])[CH:20]=1>C(Cl)(Cl)Cl>[Br:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:7][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][C:4]=2[F:10])=[O:24])=[C:21]([N+:28]([O-:30])=[O:29])[CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3770848(4-Bromo-2-fluorophenyl)methanamineHCID 189198804-Bromo-2-nitrobenzoyl chloride

Product 1

HCID 144589874-bromo-N-(4-bromo-2-fluorobenzyl)-2-nitrobenzamideYield 81.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 4-bromo-2-fluorobenzylamine (2.3 g) and triethylamine (1.55 ml) in chloroform (40 ml) was added dropwise a solution of 4-bromo-2-nitrobenzoyl chloride (2.69 g) in chloroform (10 ml) at 0° C. with stirring and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was washed in turn with diluted aqueous hydrochloric acid and water, and then dried. Evaporation of the solvent followed by recrystallization from diethyl ether gave 4-bromo-N-(4-bromo-2-fluorobenzyl)-2-nitrobenzamide (3.60 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. washThe reaction mixture was washed in turn with diluted aqueous hydrochloric acid and water
  3. customdried
  4. customEvaporation of the solvent
  5. customfollowed by recrystallization from diethyl ether

Sources & evidence

ORD record
ord-acb49f0dbaa5489e8e7915b30e3a5ec7
Source dataset
uspto-grants-1989_11
Patent number
US04883800

Linked notes

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