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

HRID 1065546Notes

Reaction equation

HRID 1065546 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 brooder 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. temperatureto reflux from the
  2. temperatureheat of the lamp
  3. filtrationThe reaction mixture was then filtered
  4. washthe filter cake was washed with three portions of carbon tetrachloride
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f953b869395f4412af2a1a3adfba4b84
Source dataset
uspto-grants-1982_05
Patent number
US04329518

Reaction notes

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