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

HRID 1995139Notes

Reaction equation

HRID 1995139 reaction equation
[Cl: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.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:33][CH2:8][C:7]1[C:2]([Cl: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

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22013535HCID 22013535, compound

Product 1

HCID 202706313-(Bromomethyl)-2-chloro-1,1'-biphenylYield 92.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred solution of 2-chloro-3-methyl-[1,1'-biphenyl] (0.5 g, 0.0023 mole) in 8 ml of carbon tetrachloride was irradiated and heated to reflux with a 250 watt brooder lamp. A small amount of benzoyl peroxide was added and the reaction mixture refluxed for ten minutes. A second portion of benzoyl peroxide (total 0.01 g) was added, followed by N-bromosuccinimide (0.43 g, 0.0024 mole). The stirred reaction mixture was irradiated for 16 hours, then cooled, and then filtered. The filter cake was rinsed with carbon tetrachloride and the combined filtrates washed with aqueous saturated 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-chloro-[1,1'-biphenyl] (0.6 g) as an oil.

Workup

  1. temperatureheated
  2. temperatureto reflux with a 250 watt brooder lamp
  3. temperaturethe reaction mixture refluxed for ten minutes
  4. customThe stirred reaction mixture
  5. customwas irradiated for 16 hours
  6. temperaturecooled
  7. filtrationfiltered
  8. washThe filter cake was rinsed with carbon tetrachloride
  9. washthe combined filtrates washed with aqueous saturated sodium chloride solution
  10. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ec0c588987724064a319fd8c5d66eeec
Source dataset
uspto-grants-1983_09
Patent number
US04402973

Reaction notes

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