Oxygen → 1-(Bromodifluoromethyl)-4-(trifluoromethoxy)benzene

HRID 1913786Notes

Reaction equation

HRID 1913786 reaction equation
[F:1][CH:2]([F:14])[C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][CH:4]=1.[Br:15]N1C(=O)CCC1=O.O=O>ClC(Cl)(Cl)Cl>[Br:15][C:2]([F:1])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]([F:11])([F:12])[F:13])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 977OxygenHCID 67184N-bromobutanimideHCID 46311762HCID 46311762, compound

Product 1

HCID 591805161-(Bromodifluoromethyl)-4-(trifluoromethoxy)benzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2.38 g (11.22 mmol) of 1-(difluoromethyl)-4-(trifluoromethoxy)benzene and 6.19 g (34.78 mmol) of N-bromosuccinimide (NBS) in 25 ml of tetrachloromethane is irradiated with exclusion of oxygen using a sun lamp. During this, the solvent reaches its boiling point. It is irradiated under reflux for 48 hours. The mixture is then allowed to cool to room temperature, precipitated succinimide is filtered off, and the filtrate is evaporated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane). 1.73 g (5.94 mmol, 53% of theory) of a yellowish oil are obtained.

Workup

  1. customIt is irradiated
  2. temperatureunder reflux for 48 hours
  3. customprecipitated succinimide
  4. filtrationis filtered off
  5. customthe filtrate is evaporated to dryness
  6. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane)
  7. custom1.73 g (5.94 mmol, 53% of theory) of a yellowish oil are obtained

Sources & evidence

ORD record
ord-1c22f1c9d5e04ddeab63af85d76ea279
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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