N-bromobutanimide → 4-Bromomethyl-3-fluorobiphenyl

HRID 1276933Notes

Reaction equation

HRID 1276933 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 161275023-Fluoro-4-methylbiphenyl

Product 1

HCID 186808134-Bromomethyl-3-fluorobiphenylYield 97.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 6.00 g of 3-fluoro-4-methylbiphenyl, 5.73 g of N-bromosuccinimide, 0.075 g of 2,2'-azobisisobutylonitrile and 120 ml of carbon tetrachloride was heat-refluxed for 5 hours. The reaction solution was washed with water, and the organic layer was concentrated. The resulting residue was purified through silica-gel column chromatography (eluent: a mixture of hexane and ethyl acetate at a ratio of 9:1) to give 8.30 g of oily 4-bromomethyl-3-fluorobiphenyl.

Workup

  1. temperaturewas heat-refluxed for 5 hours
  2. washThe reaction solution was washed with water
  3. concentrationthe organic layer was concentrated
  4. customThe resulting residue was purified through silica-gel column chromatography (eluent
  5. additiona mixture of hexane and ethyl acetate at a ratio of 9:1)

Sources & evidence

ORD record
ord-09a8d581ba6a4881b8f5930a862bade0
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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