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

HRID 1363287Notes

Reaction equation

HRID 1363287 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 98.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2-methyl-4-trifluoromethyl-furan (J. Heterocyclic Chemistry 1970, 7, 269-272) (340 mg, 2.26 mmol), N-bromosuccinimide (423 mg, 2.38 mmol) and azobisisobutyronitrile (19 mg, 0.11 mmol) in carbon tetrachloride (10 mL) was refluxed for 1.5 h, then allowed to cool to rt and filtered through a cotton plug. The solvent was evaporated to give 2-(bromomethyl)-4-(trifluoromethyl)furan as an orange oil (508 mg, 98%). The product was pure enough by proton NMR that no further purification was necessary. 1H NMR (400 MHz, CDCl3) δ ppm 4.46 (d, J=0.44 Hz, 2H), 6.56 (d, J=0.49 Hz, 1H), 7.77 (m, 1H).

Workup

  1. filtrationfiltered through a cotton plug
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-8e5e923cb7ad4cc294c47aecc01b8d1a
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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