2-Methoxyaniline → 3-bromo-4-chloro-N-(2-methoxy-phenyl)-benzamide

HRID 1848568Notes

Reaction equation

HRID 1848568 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].C(N(CC)CC)C.[CH3:19][O:20][C:21]1[C:22]([NH2:27])=[CH:23][CH:24]=[CH:25][CH:26]=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[O:20][CH3:19])=[O:6]

Participants

5

Reactant 3

HCID 70002-MethoxyanilineHCID 8471TriethylamineHCID 202297303-Bromo-4-chlorobenzoyl chloride

Product 1

HCID 686027883-bromo-4-chloro-N-(2-methoxy-phenyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Bromo-4-chloro-benzoyl chloride in DCM (200 mL) was cooled in an ice bath and triethylamine (11.1 mol, 80 mmol) was added slowly, followed by the drop-wise addition of o-anisidine (4.5 mL, 40 mmol) in DCM (50 mL). At this time the ice bath was removed and the mixture was stirred for 12 hrs, followed by partition between DCM and water. The organic layer was washed with 1 N HCl, saturated NaHCO3, brine and dried over MgSO4. Concentration of the filtrate yielded 3-bromo-4-chloro-N-(2-methoxy-phenyl)-benzamide as a pinkish solid (13.5 g).

Workup

  1. customAt this time the ice bath was removed
  2. customby partition between DCM and water
  3. washThe organic layer was washed with 1 N HCl, saturated NaHCO3, brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-b9f1876a54d34293997114b47e72c798
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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