Triethylamine → HCID 60769583, compound

HRID 1049922Notes

Reaction equation

HRID 1049922 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5](O)=[O:6].Cl.[CH3:13][NH:14][O:15][CH3:16].CCN(CC)CC>S(Cl)(Cl)=O.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5]([N:14]([O:15][CH3:16])[CH3:13])=[O:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27733393-Bromo-5-fluorobenzoic acid

Product 1

HCID 60769583HCID 60769583, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 3-bromo-5-fluorobenzoic acid (commercially available) (10.0 g, 45.7 mmol) in thionyl chloride (80 mL) was heated at reflux for 2 hours. Thionyl chloride was removed under reduced pressure and the residue was added to solution of N,O-dimethylhydroxylamine hydrochloride (5.32 g, 54.8 mmol) and Et3N (10.1 g, 0.1 mol) in DCM (300 mL) dropwise at 0° C. After the reaction mixture was stirred at r.t. overnight, it was washed with water (3×100 mL), brine, dried over anhydrous Na2SO4 and concentrated. The colorless oil was used in next step without further purification (11.0 g, yield: 95%).

Workup

  1. temperatureat reflux for 2 hours
  2. customThionyl chloride was removed under reduced pressure
  3. washit was washed with water (3×100 mL), brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe colorless oil was used in next step without further purification (11.0 g, yield: 95%)

Sources & evidence

ORD record
ord-900b1f9fbe534284b54d9e8e67bd9914
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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