Benzoyl Peroxide → 3-(Bromomethyl)-2-fluoro-1,1'-biphenyl

HRID 485560Notes

Reaction equation

HRID 485560 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:33]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:33][CH2:8][C:7]1[C:2]([F:1])=[C:3]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 202706122-Fluoro-3-methyl-1,1'-biphenyl

Product 1

HCID 202706573-(Bromomethyl)-2-fluoro-1,1'-biphenylYield 95.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred solution of 2-fluoro-3-methyl-[1,1'-biphenyl] (1.5 g, 0.00805 mole) in 25 ml of carbon tetrachloride was irradiated and heated at reflux with a 250 watt brooder lamp. Benzoyl peroxide (0.2 g) was added to the reaction mixture, followed by N-bromosuccinimide (1.46 g, 0.00805 mole). After a total of 21 hours of irradiation, the reaction mixture was cooled, filtered, and the filter cake rinsed with carbon tetrachloride. The combined filtrates were washed with saturated aqueous sodium chloride solution. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to give 3-bromomethyl-2-fluoro-[1,1'-biphenyl] (2.03 g) as an oil.

Workup

  1. temperatureheated
  2. temperatureat reflux with a 250 watt brooder lamp
  3. customAfter a total of 21 hours of irradiation
  4. temperaturethe reaction mixture was cooled
  5. filtrationfiltered
  6. washthe filter cake rinsed with carbon tetrachloride
  7. washThe combined filtrates were washed with saturated aqueous sodium chloride solution
  8. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-573fd5a997f34b10a29aeb99641e3039
Source dataset
uspto-grants-1985_08
Patent number
US04536591

Reaction notes

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