Dichloromethane → 4-(Trifluoromethyl)cinnamoyl chloride

HRID 2109744Notes

Reaction equation

HRID 2109744 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9](O)=[O:10])=[CH:5][CH:4]=1.C(Cl)[Cl:17].S(Cl)(Cl)=O>CN(C=O)C>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6](/[CH:7]=[CH:8]/[C:9]([Cl:17])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 749403-[4-(Trifluoromethyl)phenyl]prop-2-enoic acid

Product 1

HCID 111072914-(Trifluoromethyl)cinnamoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To a 500 mL round-bottomed flask was added 4-(trifluoromethyl)cinnamic acid (231 mL, 116 mmol), DCM (7.44 mL, 116 mmol), thionyl chloride (17.7 mL, 243 mmol), and a few drops of DMF. The resulting mixture was stirred at reflux for about 1.5 hours and followed by LCMS (MeOH quench). Once no starting material was present, the solvents were reduced and the oil was used immediately in the next step.

Workup

  1. temperatureat reflux for about 1.5 hours
  2. customfollowed by LCMS (MeOH quench)

Sources & evidence

ORD record
ord-eec0b5a7035c485eaa5261c456932db3
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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