N-bromobutanimide → alpha-Bromopentafluorobenzyl fluoride

HRID 894348Notes

Reaction equation

HRID 894348 reaction equation
[F:1][C:2]1[C:7]([CH2:8][F:9])=[C:6]([F:10])[C:5]([F:11])=[C:4]([F:12])[C:3]=1[F:13].[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:14][CH:8]([F:9])[C:7]1[C:2]([F:1])=[C:3]([F:13])[C:4]([F:12])=[C:5]([F:11])[C:6]=1[F:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12701527Pentafluorobenzyl fluoride

Product 1

HCID 20507331alpha-Bromopentafluorobenzyl fluoride

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of pentafluorobenzyl fluoride (0.37 g), N-bromosuccinimide (0.36 g) and dry carbon tetrachloride (30 ml) was heated under reflux and irradiated with ultra violet light for a period of 4 hr. The reaction mixture was cooled, the insoluble material was removed by filtration and the solvent was removed by distillation under reduced pressure to give α-bromopentafluorobenzyl fluoride. The product was characterised by p.m.r. spectroscopy. Chemical shift δ ppm (solvent CDCl3): 7.63(d, J=48Hz).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customirradiated with ultra violet light for a period of 4 hr
  4. temperatureThe reaction mixture was cooled
  5. customthe insoluble material was removed by filtration
  6. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-9a786a0c7515418bb9a0910a14b0abcf
Source dataset
uspto-grants-1981_08
Patent number
US04283414

Reaction notes

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