Benzoyl Peroxide → HCID 59151288, compound

HRID 2365162Notes

Reaction equation

HRID 2365162 reaction equation
[Br:1][C:2]1[C:3]([CH3:15])=[C:4]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:6][CH:7]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:34]Br>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.[W]>[Br:1][C:2]1[C:3]([CH2:15][Br:34])=[C:4]([NH:8][C:9](=[O:14])[C:10]([F:11])([F:13])[F:12])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 7187Benzoyl PeroxideHCID 24408BromineHCID 86638092N-(3-Bromo-2-methylphenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 59151288HCID 59151288, compound

Reagents, catalysts & solvents 3

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(3-bromo-2-methyl-phenyl)-2,2,2-trifluoro-acetamide (2.1 g, 7.4 mmol) and benzoyl peroxide (100 mg) in carbon tetrachloride (50 mL) was heated to reflux under irradiation (150 W tungsten lamp). A solution of bromine (0.55 mL, 10.4 mmol) in carbon tetrachloride (3 mL) was then added drop-wise to the refluxing solution, and heating was pursued for 16 h. The reaction mixture was left to cool to RT and diluted with DCM. The organic layer was washed with sodium thiosulfate, and evaporated to dryness to give N-(3-bromo-2-bromomethyl-phenyl)-2,2,2-trifluoro-acetamide as a brown residue which was used without further purification (2.9 g).

Workup

  1. temperatureheating
  2. waitThe reaction mixture was left
  3. washThe organic layer was washed with sodium thiosulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-4339ac566ef44ca793dc15b2971db914
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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