Carbon Tetrachloride → 1,1'-Biphenyl, 4-ethenyl-2-fluoro-

HRID 1065533

Reaction equation

HRID 1065533 reaction equation
C(Cl)(Cl)(Cl)Cl.[F:6][C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.BrN1C(=O)CCC1=O.[OH-].[K+]>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(O)C>[F:6][C:7]1[CH:12]=[C:11]([CH:13]=[CH2:14])[CH:10]=[CH:9][C:8]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 14797Potassium HydroxideHCID 67184N-bromobutanimideHCID 14903264-Ethyl-2-fluoro-1,1'-biphenyl

Product 1

HCID 114241661,1'-Biphenyl, 4-ethenyl-2-fluoro-Yield 55.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 702EthanolSolvent

Procedure

In 750 ml. of carbon tetrachloride was dissolved 10 g of 2-fluoro-4-ethylbiphenyl. Then to the solution were added 10 g of N-bromosuccinimide and 0.1 g of benzoyl peroxide. After cooling, a solid substance was filtered off, and from the filtrate containing α-(2-fluoro-4-biphenylyl)ethyl bromide was distilled off the carbon tetrachloride. The residue thus obtained was dissolved in 500 ml. of ethyl alcohol, and then added with 17 g of potassium hydroxide. The resultant mixture was refluxed under heating for 1 hour. After cooling, the reaction mixture was poured into 2.5 l. of water, and then subjected to extraction with benzene. The benzene layer was washed with water, and dried with magnesium sulfate. The benzene in the layer was distilled off, and the resulting residue was subjected to column chromatography. From hexane eluate was obtained 5.5 g of 2-fluoro-4-vinylbiphenyl.

Workup

  1. temperatureAfter cooling
  2. filtrationa solid substance was filtered off
  3. additionfrom the filtrate containing α-(2-fluoro-4-biphenylyl)ethyl bromide
  4. distillationwas distilled off the carbon tetrachloride
  5. customThe residue thus obtained
  6. dissolutionwas dissolved in 500 ml
  7. temperatureunder heating for 1 hour
  8. temperatureAfter cooling
  9. additionthe reaction mixture was poured into 2.5 l
  10. extractionof water, and then subjected to extraction with benzene
  11. washThe benzene layer was washed with water
  12. dry with materialdried with magnesium sulfate
  13. distillationThe benzene in the layer was distilled off

Sources & evidence

ORD record
ord-6d1c0c0891be49f1bf021e2c2febd442
Source dataset
uspto-grants-1982_05
Patent number
US04329507

Linked notes

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