Hydrochloric Acid → Bromopentafluorobenzene

HRID 1600430Notes

Reaction equation

HRID 1600430 reaction equation
N#N.[F:3][C:4]1[C:9]([F:10])=[C:8]([F:11])[C:7]([F:12])=[C:6]([F:13])[C:5]=1F.C([Mg][Br:18])C.BrBr.Cl>C(Cl)Cl.C1COCC1>[C:5]1([Br:18])[C:6]([F:13])=[C:7]([F:12])[C:8]([F:11])=[C:9]([F:10])[C:4]=1[F:3]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 9805HexafluorobenzeneHCID 24408BromineHCID 178418443HCID 178418443, compound

Product 1

HCID 9578BromopentafluorobenzeneYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 2 l, N2 purged flask were combined hexafluorobenzene (145 g), FeCl2 (0.8 g) and THF (600 ml). The solution was cooled to 0°-5° C., and ethyl magnesium bromide (3.12M in Et2O, 500 ml) was then added dropwise. After the addition was complete, the reaction mixture was stirred for one-half hour. A solution of bromine (125g) n methylene chloride (250 ml) was then added dropwise to the cold (0°-5° C.) reaction mixture. After stirring 15 minutes, 4N HCl was added until all solids were dissolved. The two phases were separated and the organics were washed sequentially with water, aqueous sodium bicarbonate and brine. After drying over sodium sulfate, the mixture was distilled providing 160 g of C6F5Br (83% yield).

Workup

  1. temperatureThe solution was cooled to 0°-5° C.
  2. additionAfter the addition
  3. stirringAfter stirring 15 minutes
  4. dissolutionwere dissolved
  5. customThe two phases were separated
  6. washthe organics were washed sequentially with water, aqueous sodium bicarbonate and brine
  7. dry with materialAfter drying over sodium sulfate
  8. distillationthe mixture was distilled

Sources & evidence

ORD record
ord-fcfe8161e3dc4e6dbfb9f7539d287b23
Source dataset
uspto-grants-1998_04
Patent number
US05744656

Reaction notes

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