Fluorobenzene → HCID 15571161, compound

HRID 1759370Notes

Reaction equation

HRID 1759370 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.BrBr>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 10008FluorobenzeneHCID 24408BromineHCID 1371853-Fluorophenylacetone

Product 1

HCID 15571161HCID 15571161, compound

Procedure

A solution of 16.5 g. or m-fluorophenyl-2-propanone [Z. Eckstein and J. Plenkiewicz, Rocznik. Chem., 37, 907 (1963)] in 70 ml. of fluorobenzene is cooled and stirred as 5.5 ml. of bromine are added dropwise. Argon gas is bubbled through the mixture for one hour. The solution is then added dropwise to a mixture of 29.6 g. of aluminum chloride and 70 ml. of fluorobenzene, stirred at 80°-90° C. Stirring is continued at this temperature for one hour then the mixture is poured into ice and 45 ml. of concentrated hydrochloric acid. Toluene is added, the organic layer is separated, washed with dilute sodium hydroxide and then water and distilled, giving the desired product as a liquid, b.p. 106°-112° C./0.15 mm.

Workup

  1. customArgon gas is bubbled through the mixture for one hour
  2. additionThe solution is then added dropwise to a mixture of 29.6 g
  3. stirringof fluorobenzene, stirred at 80°-90° C
  4. stirringStirring
  5. additionthe mixture is poured into ice and 45 ml
  6. additionToluene is added
  7. customthe organic layer is separated
  8. washwashed with dilute sodium hydroxide
  9. distillationwater and distilled

Sources & evidence

ORD record
ord-ada32fbb1f274c669efb77e97d30a34d
Source dataset
uspto-grants-1982_07
Patent number
US04340734

Reaction notes

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