Dimethylformamide → 1-(3-Chloroprop-1-enyl)-3-(trifluoromethyl)benzene

HRID 410146Notes

Reaction equation

HRID 410146 reaction equation
CN(C)C=O.[F:6][C:7]([F:19])([F:18])[C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH2:16]O)[CH:11]=[CH:12][CH:13]=1.S(Cl)([Cl:22])=O>ClCCl>[Cl:22][CH2:16][CH:15]=[CH:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:7]([F:19])([F:18])[F:6])[CH:9]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 545026543-(3-Trifluoromethylphenyl)-2-propene-1-ol

Product 1

HCID 534418431-(3-Chloroprop-1-enyl)-3-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

Dimethylformamide (5 mL) was added to a solution of 3-[3-(trifluoromethyl)phenyl]prop-2-en-1-ol (50 g) in dichloromethane (500 mL) at 0 to 5° C. Thionyl chloride (44.2 g) was slowly added to the above mixture maintaining the temperature at about 0 to 5° C. The reaction mixture was stirred at 0 to 5° C. for 1-2 hours. After completion of the reaction, the mixture was quenched with ice-chilled de-ionized water (250 mL) at 0-10° C. and stirred for 30 minutes. Organic layer was separated, washed twice with a solution of sodium chloride (10%; 250 mL) and concentrated under vacuum to give 1-[3-chloroprop-1-en-1-yl]-3-(trifluoromethyl)benzene.

Workup

  1. customAfter completion of the reaction
  2. customthe mixture was quenched with ice-
  3. temperaturechilled de-ionized water (250 mL) at 0-10° C.
  4. stirringstirred for 30 minutes
  5. customOrganic layer was separated
  6. washwashed twice with a solution of sodium chloride (10%; 250 mL)
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-75829980257e464b9eec5594a43f4d03
Source dataset
uspto-grants-2014_06
Patent number
US08759586B2

Reaction notes

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