3-(Trifluoromethyl)phenol → HCID 14512541, compound

HRID 258327Notes

Reaction equation

HRID 258327 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[F:19][C:20](=[CH2:24])[C:21](Cl)=[O:22]>C(Cl)Cl>[F:19][C:20](=[CH2:24])[C:21]([O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)=[O:22]

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 8471TriethylamineHCID 27833352-Fluoroacryloyl chloride

Product 1

HCID 14512541HCID 14512541, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

27.5 g (0.169 mol) of 3-trifluoromethylphenol were dissolved in 100 ml of anhydrous methylene dichloride, and 17.1 g (0.169 mol) of triethylamine were added in portions to the solution; 20 g (0.184 mol) of α-fluoroacryloyl chloride (obtained in accordance with example 1c) were then added dropwise, at a temperature of 5° C., with stirring and in the course of 20 minutes, and the reaction mixture was stirred for a further 60 minutes at the same temperature. The solid formed was filtered off and washed with 30 ml of methylene dichloride. The mixture of filtrate and wash solution was distilled, after adding 0.01 g of hydroquinone monomethyl ether. 27 g (68% of theory) of 3-trifluoromethylphenyl α-fluoroacrylate were obtained, boiling point 78° to 79° C. (under 4 mbar).

Workup

  1. stirringthe reaction mixture was stirred for a further 60 minutes at the same temperature
  2. customThe solid formed
  3. filtrationwas filtered off
  4. washwashed with 30 ml of methylene dichloride
  5. additionThe mixture of filtrate
  6. washwash solution
  7. distillationwas distilled
  8. additionafter adding 0.01 g of hydroquinone monomethyl ether

Sources & evidence

ORD record
ord-38e232f4472844959dfb9e3b4691fbbe
Source dataset
uspto-grants-1993_11
Patent number
US05266668

Reaction notes

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