N-bromobutanimide → 1-(Bromomethyl)-4-(1,1,2,2-tetrafluoroethoxy)benzene

HRID 1610262Notes

Reaction equation

HRID 1610262 reaction equation
[F:1][C:2]([F:14])([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]([F:14])([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][Br:15])=[CH:9][CH:8]=1)[CH:3]([F:4])[F:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 74439alpha,alpha,beta,beta-Tetrafluoro-p-methylphenetole

Product 1

HCID 222617841-(Bromomethyl)-4-(1,1,2,2-tetrafluoroethoxy)benzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 4-(1,1,2,2-tetrafluoroethoxy)toluene (6.73 g, 32.3 mmol), N-bromosuccinimide (5.75 g, 32.3 mmol) and 2,2-azobis(isobutyronitrile) (0.2 g) in carbon tetrachloride (30 ml) was heated under reflux for 0.5 hr. After cooling the reaction solution to room temperature, the white precipitate as removed by filtration and the precipitate was washed with diethyl ether. The solvent of the collected filtrate was evaporated under reduced pressure to give a crude product of 4-(1,1,2,2-tetrafluoroethoxy)benzyl bromide as a pale-yellow liquid.

Workup

  1. temperatureunder reflux for 0.5 hr
  2. customthe white precipitate as removed by filtration
  3. washthe precipitate was washed with diethyl ether
  4. customThe solvent of the collected filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cb18a0d76d044ff894102acc3746e80d
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…