4-Bromoaniline → N-(4-Bromophenyl)benzofuran-2-carboxamide

HRID 29282

Reaction equation

HRID 29282 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[O:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[C:10]1[C:18](Cl)=[O:19].C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18]([C:10]2[O:9][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH:11]=2)=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 8471TriethylamineHCID 389492-Benzofurancarbonyl chloride

Product 1

HCID 869135N-(4-Bromophenyl)benzofuran-2-carboxamideYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1.72 g of 4-bromoaniline was added to 1.89 g of benzofuran-2-carboxylic acid chloride in 35 mL of dichloromethane cooled in ice bath, followed by the addition of 4.9 mL of triethylamine. The reaction was stirred at room temperature overnight and then diluted with dichloromethane. The dichloromethane layer was washed with water, 1N HCl, water and brine, dried over Na2SO4, filtered, and concentrated in vacuo to provide 2.61 g of N-(4-bromophenyl)-1-benzofuran-2-carboxamide as a yellow solid. Yield 72%. m.p. 178-180° C.; MS: 314.1(M−H)−.

Workup

  1. temperaturecooled in ice bath
  2. washThe dichloromethane layer was washed with water, 1N HCl, water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5885f19d0c34a63b1f37077c29399fa
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Linked notes

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