Trichloroacetyl chloride → HCID 68709804, compound

HRID 2067936Notes

Reaction equation

HRID 2067936 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[CH2:5])[CH3:2].[Cl:13][C:14]([Cl:19])([Cl:18])[C:15](Cl)=[O:16]>N1C=CC=CC=1.C(Cl)Cl>[Cl:13][C:14]([Cl:19])([Cl:18])[C:15](=[O:16])[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:6]1[CH:7]=[CH:8][C:9]([F:12])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 68707181HCID 68707181, compound

Product 1

HCID 68709804HCID 68709804, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 7.49 g 1-(1-Ethoxy-vinyl)-4-Fluorobenzene in 3.6 mL of Pyridine was added at 0° C. to 8.19 g of Trichloroacetyl chloride. The suspension was diluted with 15 ml of dry methylene chloride and stirred at room temperature overnight. The resulting dark brown suspension was concentrated in vaccuo, filtered over a silica gel column with a 9:1 mixture of Heptane and Ethyl acetate as eluant. One obtains after concentration 28 g of a reddish brown oil which was repurified by chromatography on silica gel using a 19:1 mixture of Heptane and Ethyl acetate as eluant. The obtained brown oil (10.15 g) was directly used in the next step.

Workup

  1. concentrationThe resulting dark brown suspension was concentrated in vaccuo
  2. filtrationfiltered over a silica gel column with a 9:1 mixture of Heptane and Ethyl acetate as eluant
  3. customOne obtains after concentration 28 g of a reddish brown oil which
  4. customwas repurified by chromatography on silica gel using
  5. additiona 19:1 mixture of Heptane and Ethyl acetate as eluant

Sources & evidence

ORD record
ord-1f944542ec6240d38d4c6de0dc484b5f
Source dataset
uspto-grants-2012_10
Patent number
US08293916B2

Reaction notes

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