N-bromobutanimide → Methyl 4-(bromomethyl)-3-(trifluoromethyl)benzoate

HRID 2039980Notes

Reaction equation

HRID 2039980 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:6]([O:8][CH3:9])=[O:7].[Br:16]N1C(=O)CCC1=O.C(OOCC1C=CC=CC=1)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:13][C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:2]([F:14])([F:15])[F:1]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 11229634Benzyl PeroxideHCID 11952921Methyl 4-methyl-3-(trifluoromethyl)benzoate

Product 1

HCID 57443327Methyl 4-(bromomethyl)-3-(trifluoromethyl)benzoateYield 88%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A reactor is charged with 1 g (4.6 mmol) of the compound obtained in step 1, 0.97 g (5.5 mmol) of N-bromosuccinimide, 133 mg (0.55 mmol) of benzyl peroxide and 25 ml of carbon tetrachloride. The mixture is heated for 4 hours at reflux. The solvent is evaporated under reduced pressure and 100 ml of a saturated sodium bicarbonate solution is added. The solution obtained is extracted with 3*30 ml ethyl acetate. The organic phases are combined, dried on sodium sulphate and evaporated under reduced pressure to give the expected product (1.2 g, 88%).

Workup

  1. temperatureThe mixture is heated for 4 hours
  2. temperatureat reflux
  3. customThe solvent is evaporated under reduced pressure and 100 ml of a saturated sodium bicarbonate solution
  4. additionis added
  5. customThe solution obtained
  6. extractionis extracted with 3*30 ml ethyl acetate
  7. customdried on sodium sulphate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5bf4e393be844e13b19d167f2911719e
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

Loading…