4-Fluorobenzoyl chloride → HCID 21704863, compound

HRID 1595235Notes

Reaction equation

HRID 1595235 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[Cl:7].[F:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1>ClCCl>[Br:1][C:2]1[S:3][C:4]([C:13](=[O:14])[C:12]2[CH:16]=[CH:17][C:9]([F:8])=[CH:10][CH:11]=2)=[CH:5][C:6]=1[Cl:7]

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 27245612-Bromo-3-chlorothiophene

Product 1

HCID 21704863HCID 21704863, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
18 °C

Procedure

Ferric chloride (301.2 g) was added to a stirred solution of 2-bromo-3-chlorothiophene (148.5 g) and 4-fluorobenzoyl chloride (169.7 g) in dichloromethane (2230 ml), cooled to 18° C. in an icetwater bath. The temperature of the reaction mixture rose to 22° C. and was then cooled to 12° C. Cooling was removed and the reaction mixture was stirred for a further 50 min during which time the internal temperature rose to 16° C. The reaction mixture was re-cooled to 10° C., water (700 ml) was added carefully, keeping the internal temperature below 15° C., and the mixture was then stirred for 1 h. The dichloromethane layer was separated and the aq layer was washed with dichloromethane. The combined dichloromethane layer was washed with water and saturated sodium bicarbonate solution. The dichloromethane was separated and the aq. layer filtered through dicalite and extracted with dichloromethane. The extract was washed with water, dried (Na2SO4) and evaporated to dryness to give 2-bromo-3-chloro-5-(4-fluorobenzoyl)-thiophene as a solid (233.3 g).

Workup

  1. customrose to 22° C.
  2. temperaturewas then cooled to 12° C
  3. temperatureCooling
  4. customwas removed
  5. customrose to 16° C
  6. temperatureThe reaction mixture was re-cooled to 10° C.
  7. additionwater (700 ml) was added carefully
  8. customthe internal temperature below 15° C.
  9. stirringthe mixture was then stirred for 1 h
  10. customThe dichloromethane layer was separated
  11. washthe aq layer was washed with dichloromethane
  12. washThe combined dichloromethane layer was washed with water and saturated sodium bicarbonate solution
  13. customThe dichloromethane was separated
  14. filtrationthe aq. layer filtered through dicalite
  15. extractionextracted with dichloromethane
  16. washThe extract was washed with water
  17. dry with materialdried (Na2SO4)
  18. customevaporated to dryness

Sources & evidence

ORD record
ord-dce4d0ea702b48f691f9d89b834b42a3
Source dataset
uspto-grants-2001_09
Patent number
US06288085B1

Reaction notes

Loading…