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

HRID 1388818Notes

Reaction equation

HRID 1388818 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 mixture of 3-chloro-2-methyl[1,1'-biphenyl] (10.4 grams, 0.051 mole) and N-bromosuccinimide (9.2 grams, 0.052 mole) in carbon tetrachloride (150 ml) was heated and irradiated with an infrared lamp for two hours. The mixture was cooled and filtered. The filtrate was evaporated under reduced pressure to give a quantitative yield of 2-bromomethyl-3-chloro[1,1'-biphenyl] as a yellow oil.

Workup

  1. temperaturewas heated
  2. customirradiated with an infrared lamp for two hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-40b1820f400949cfa5d1c71c1874b10b
Source dataset
uspto-grants-1984_02
Patent number
US04433182

Reaction notes

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