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

HRID 1065577Notes

Reaction equation

HRID 1065577 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-1c15af0ff7444014af1dbb13d0d7b3d0
Source dataset
uspto-grants-1982_05
Patent number
US04329518

Reaction notes

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