Pyridine → 4-(Trifluoromethyl)cinnamoyl chloride

HRID 342613Notes

Reaction equation

HRID 342613 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]([F:19])([F:18])[C:7]1[CH:17]=[CH:16][C:10](/[CH:11]=[CH:12]/[C:13](O)=[O:14])=[CH:9][CH:8]=1.N1C=CC=CC=1>C(Cl)Cl>[F:5][C:6]([F:19])([F:18])[C:7]1[CH:17]=[CH:16][C:10](/[CH:11]=[CH:12]/[C:13]([Cl:3])=[O:14])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 6880704-(Trifluoromethyl)cinnamic acid

Product 1

HCID 111072914-(Trifluoromethyl)cinnamoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (335 ml, 4.6 mmol) was added at 0° C. to 4-trifluoromethyl-E-cinnamic acid (1 g, 4.6 mmol) and pyridine (375 ml, 4.6 mmol) in dry CH2Cl2. The mixture was then stirred for 1 h without cooling, again cooled to 0° C. and filtered with the exclusion of moisture. The filtrate (10 ml) contained the title compound and was used in aliquots for the next reaction step.

Workup

  1. temperaturewithout cooling
  2. filtrationfiltered with the exclusion of moisture
  3. customwas used in aliquots for the next reaction step

Sources & evidence

ORD record
ord-548f034edc534529847ea7bcc3e082ba
Source dataset
uspto-grants-1999_01
Patent number
US05859025

Reaction notes

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