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

HRID 448856Notes

Reaction equation

HRID 448856 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-e78b4b658e23410f91af610bfb887ea1
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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