N,O-Dimethylhydroxylamine → HCID 53417458, compound

HRID 2175803Notes

Reaction equation

HRID 2175803 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5](O)=[O:6].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:24][O:25][NH:26][CH3:27]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([N:26]([O:25][CH3:24])[CH3:27])=[O:6]

Participants

5

Reactant 3

HCID 14232N,O-DimethylhydroxylamineHCID 682631,1'-CarbonyldiimidazoleHCID 705093-Bromo-4-fluorobenzoic acid

Product 1

HCID 53417458HCID 53417458, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-4-fluorobenzoic acid (100 g, 0.456 mol) and CDI (77.2 g, 0.547 mol) in 1 L of dry DCM was stirred at r.t. for 30 min and then O,N-dimethyl-hydroxylamine (53.4 g, 0.547 mol) was added. The resulted mixture was stirred overnight. The solvents were removed under vacuum and the residue was purified via column chromatograph to afford 3-bromo-4-fluoro-N-methoxy-N-methylbenzamide.

Workup

  1. customThe solvents were removed under vacuum
  2. customthe residue was purified via column chromatograph

Sources & evidence

ORD record
ord-51a65cfe92e347d1b1859677ce613539
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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