N-bromobutanimide → 2-(Bromomethyl)-4-(trifluoromethyl)furan

HRID 1654112Notes

Reaction equation

HRID 1654112 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[C:5]([C:7]([F:10])([F:9])[F:8])[CH:6]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:11][CH2:1][C:2]1[O:3][CH:4]=[C:5]([C:7]([F:10])([F:9])[F:8])[CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 218197502-Methyl-4-(trifluoromethyl)furan

Product 1

HCID 218197532-(Bromomethyl)-4-(trifluoromethyl)furanYield 60.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

6 g of the product of Stage D were refluxed for 1 and a half hours in 50 ml of carbon tetrachloride in the presence of 7.2 g of N-bromosuccinimide and 0.3 g of azobisisobutyronitrile and the mixture was allowed to return to room temperature and was filtered. The solvent was evaporated and the residue was chromatographed on silica (eluent: 98/2 ether/isopropyl ether) to obtain 5.5 g of the expected product.

Workup

  1. customto return to room temperature
  2. filtrationwas filtered
  3. customThe solvent was evaporated
  4. customthe residue was chromatographed on silica (eluent: 98/2 ether/isopropyl ether)

Sources & evidence

ORD record
ord-b3d89a00b8414e9d93c3bacac0ffbde1
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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