N-bromobutanimide → 2-(Bromomethyl)-3-chloro-1,1'-biphenyl

HRID 1065566Notes

Reaction equation

HRID 1065566 reaction equation
[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:14][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 46018323-Chloro-2-methylbiphenyl

Product 1

HCID 133207002-(Bromomethyl)-3-chloro-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred solution of 3-chloro-2-methyl-[1,1'-biphenyl] (13.5 g, 0.067 mole) and N-bromosuccinimide (11.8 g, 0.067 mole) in 125 ml of carbon tetrachloride was irradiated and heated to reflux for 61/2 hours with a 250 watt brooder lamp. The light/heat source was turned off and the reaction mixture stirred at room temperature for approximately 64 hours. The reaction mixture was again irradiated and heated for two hours with the brooder lamp. The mixture was cooled, a solid precipitate filtered off, and the filter cake washed with two 50 ml portions of carbon tetrachloride. The filtrate was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure to give 2-bromomethyl-3-chloro-[1,1'-biphenyl] as an oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 61/2 hours with a 250 watt brooder lamp
  3. customThe reaction mixture was again irradiated
  4. temperatureheated for two hours with the brooder lamp
  5. temperatureThe mixture was cooled
  6. filtrationa solid precipitate filtered off
  7. washthe filter cake washed with two 50 ml portions of carbon tetrachloride
  8. washThe filtrate was washed with saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8cfb746a038641d5b0edf08374ac0784
Source dataset
uspto-grants-1982_05
Patent number
US04329518

Reaction notes

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