1,2-Dichloroethane → 4-Bromo-3-fluoro-N-methoxy-N-methylbenzamide

HRID 216325Notes

Reaction equation

HRID 216325 reaction equation
[CH3:1][NH:2][O:3][CH3:4].[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][C:7]=1[F:15].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.C(OCC)(=O)C>[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([N:2]([O:3][CH3:4])[CH3:1])=[O:11])=[CH:8][C:7]=1[F:15]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 14232N,O-DimethylhydroxylamineHCID 757711-HydroxybenzotriazoleHCID 27733414-Bromo-3-fluorobenzoic acid

Product 1

HCID 223138234-Bromo-3-fluoro-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,O-Dimethylhydroxylamine (2.45 g, 25.1 mmol) was added to an ambient temperature solution of 4-bromo-3-fluorobenzoic acid (5 g, 22.8 mmol), EDC (5.25 g, 27.4 mmol), HOBt (4.2 g, 27.4 mmol) and NMM (12.55 mL, 114.2 mmol) in methylene chloride (50 mL). After stirring at ambient temperature overnight, the reaction mixture was poured into ethyl acetate and washed successively with saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 40-80% ethyl acetate/hexane afforded 4-bromo-3-fluoro-N-methoxy-N-methylbenzamide.

Workup

  1. washwashed successively with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0661d2005bc743949d9538c05ab109c3
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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