Hydrochloric Acid → HCID 10493986, compound

HRID 1034408Notes

Reaction equation

HRID 1034408 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.Cl>[Cl-].[Zn+2].[Cl-]>[NH2:16][C:15]1[CH:17]=[CH:18][C:12]([F:11])=[CH:13][C:14]=1[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[Br:1])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 97314-FluoroanilineHCID 235422-Bromobenzoyl chloride

Product 1

HCID 10493986HCID 10493986, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
110 °C

Procedure

A mixture of 20 g (0.15 mol) of zinc chloride and 50 g (0.23 mol) of 2-bromobenzoyl chloride was heated to 110° C. 4-Fluoroaniline, 13 g (0.12 mol) Was added over a period of 2 minutes, raising the temperature of the mixture to 160° C. This mixture was then heated and stirred for 3 hours at 210°-220° C. After cooling to 140° C., 200 mL of hot 3N hydrochloric acid was added cautiously. The mixture was stirred and heated to reflux for 5 minutes and the aqueous phase was decanted from the residue. This procedure was repeated twice. The residue was dissolved in 200 mL acetic acid and treated with 100 mL of 3N hydrochloric acid and 10 mL of concentrated sulfuric acid to form a mixture.

Workup

  1. temperatureraising the temperature of the mixture to 160° C
  2. temperatureThis mixture was then heated
  3. temperatureAfter cooling to 140° C.
  4. stirringThe mixture was stirred
  5. temperatureheated
  6. temperatureto reflux for 5 minutes
  7. customthe aqueous phase was decanted from the residue
  8. dissolutionThe residue was dissolved in 200 mL acetic acid
  9. additiontreated with 100 mL of 3N hydrochloric acid and 10 mL of concentrated sulfuric acid
  10. customto form a mixture

Sources & evidence

ORD record
ord-0d704a8ce6a84b5ba41c516c326ba6b1
Source dataset
uspto-grants-1994_05
Patent number
US05317018

Reaction notes

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