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

HRID 1485923Notes

Reaction equation

HRID 1485923 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-951fbedf20c74039a590d4d53130edda
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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