Water → 2-(Bromomethyl)-5-(trifluoromethyl)furan

HRID 1610328Notes

Reaction equation

HRID 1610328 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:7]([F:10])([F:9])[F:8])=[CH:5][CH:6]=1.[Br:11]N1C(=O)CCC1=O.O>C(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:11][CH2:1][C:2]1[O:3][C:4]([C:7]([F:10])([F:9])[F:8])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 109536882-Methyl-5-(trifluoromethyl)furan

Product 1

HCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanYield 78.6%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 2-methyl-5-(trifluoromethyl)furan (4 g, 26.6 mmol) in chloroform (60 ml) were added N-bromosuccinimide (5.2 g, 29.3 mmol) and 2,2′-azobis(isobutyronitrile) (220 mg, 1.33 mmol). The reaction solution was heated under reflux for 15 min. The reaction solution was cooled, poured into water (200 ml) and was extracted with chloroform. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give 2-(bromomethyl)-5-(trifluoromethyl)furan (4.79 g, 78%).

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux for 15 min
  3. temperatureThe reaction solution was cooled
  4. extractionwas extracted with chloroform
  5. washThe extract was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a54835f45fca449f8ff1660eda4ae0c1
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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