N-bromobutanimide → 3-(Bromomethyl)-2,4-difluoro-1,1'-biphenyl

HRID 2057990Notes

Reaction equation

HRID 2057990 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:8][C:7]1[C:2]([F:1])=[C:3]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:4]=[CH:5][C:6]=1[F:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 128530332,4-Difluoro-3-methyl-1,1'-biphenyl

Product 1

HCID 128530343-(Bromomethyl)-2,4-difluoro-1,1'-biphenylYield 112.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred solution of 2,4-difluoro-3-methyl[1,1'-biphenyl] (2.2 g, 0.011 mole) and N-bromosuccinimide (1.9 g, 0.011 mole) in 100 ml of carbon tetrachloride was irradiated with a 250 watt infrared lamp for 4 hours. The reaction mixture was allowed to reflux from the heat of the lamp. The reaction mixture was then filtered, and the filter cake was washed with three portions of carbon tetrachloride. The washes and filtrate were combined and evaporated under reduced pressure to give 3-bromomethyl-2,4-difluoro[1,1'-biphenyl] (3.5 g) as an oil whose nmr spectrum was consistent with that expected for the named compound.

Workup

  1. customfor 4 hours
  2. temperatureto reflux from the
  3. temperatureheat of the lamp
  4. filtrationThe reaction mixture was then filtered
  5. washthe filter cake was washed with three portions of carbon tetrachloride
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6b03e64bde704e6eaf94de3df92da838
Source dataset
uspto-grants-1980_07
Patent number
US04214004

Reaction notes

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