1-Bromo-3-fluorobenzene → HCID 14032496, compound

HRID 1722144Notes

Reaction equation

HRID 1722144 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:7]=[C:8]([Br:12])[CH:9]=[CH:10][CH:11]=1.[C:13]([N:16]1[CH2:24][CH2:23][CH:19]([C:20](Cl)=[O:21])[CH2:18][CH2:17]1)(=[O:15])[CH3:14]>>[Br:12][C:8]1[CH:9]=[CH:10][C:11]([C:20]([CH:19]2[CH2:18][CH2:17][N:16]([C:13](=[O:15])[CH3:14])[CH2:24][CH2:23]2)=[O:21])=[C:6]([F:5])[CH:7]=1

Participants

4

Reactant 3

HCID 140821-Bromo-3-fluorobenzeneHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14032496HCID 14032496, compoundYield 19%

Procedure

To a stirred suspension of 21.1 g of aluminum chloride and 63 ml of 3-fluorobromobenzene was added, portionwise, 16.0 g of 1-acetylisonipecotoyl chloride. The reaction mixture was stirred under reflux for 4 hrs. Most of the supernatant 3-fluorobromobenzene was decanted and ice water was added. The aqueous mixture was extracted with dichloromethane and the extract was washed with water, dried over anhydrous magnesium sulfate and the solvent concentrated to give an oil. The oil was triturated with ether and a solid separated out. Recrystallization of the solid from cyclohexane gave 4.9 g (19%) of product. Recrystallization from cyclohexane yield the analytical sample, mp 111°-113° C.

Workup

  1. additionwas added
  2. temperatureunder reflux for 4 hrs
  3. customMost of the supernatant 3-fluorobromobenzene was decanted
  4. additionice water was added
  5. extractionThe aqueous mixture was extracted with dichloromethane
  6. washthe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationthe solvent concentrated
  9. customto give an oil
  10. customThe oil was triturated with ether
  11. customa solid separated out
  12. customRecrystallization of the solid from cyclohexane

Sources & evidence

ORD record
ord-b5e7e6ae07634b5aa88ecb189f6821bb
Source dataset
uspto-grants-1989_08
Patent number
US04853470

Reaction notes

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