Triethylamine → 2,6-Dichloro-4-cyanophenyl alpha-fluoroacrylate

HRID 258329Notes

Reaction equation

HRID 258329 reaction equation
[F:1][C:2](=[CH2:6])[C:3](Cl)=[O:4].[Cl:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([Cl:17])[C:15]=1[OH:16])[C:11]#[N:12].C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2](=[CH2:6])[C:3]([O:16][C:15]1[C:14]([Cl:17])=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[Cl:7])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74685ChloroxynilHCID 27833352-Fluoroacryloyl chloride

Product 1

HCID 140081602,6-Dichloro-4-cyanophenyl alpha-fluoroacrylateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g (0.092 mol) of α-fluoroacryloyl chloride (obtained in accordance with example 1c) were added dropwise, at a temperature of 5° C., with stirring and in the course of 20 minutes, to a solution of 16.7 g (0.089 mol) of 3,5-dichloro-4-hydroxybenzonitrile and 9 g (0.089 mol) of triethylamine in 200 ml of anhydrous methylene dichloride, and the reaction mixture was then stirred for a further 30 minutes at the same temperature. The solid formed was filtered off and washed with 20 ml of anhydrous methylene dichloride. After 0.005 g of hydroquinone monomethyl ether had been added, the volatile constituents in the mixture of filtrate and wash solution were removed by distillation, and the residue was recrystallized from boiling n-heptane. 18.7 g (81% of theory) of 2,6-dichloro-4-cyanophenyl α-fluoroacrylate were obtained, melting point 95° to 99° C.

Workup

  1. customThe solid formed
  2. filtrationwas filtered off
  3. washwashed with 20 ml of anhydrous methylene dichloride
  4. additionAfter 0.005 g of hydroquinone monomethyl ether had been added
  5. additionthe volatile constituents in the mixture of filtrate
  6. washwash solution
  7. customwere removed by distillation
  8. customthe residue was recrystallized

Sources & evidence

ORD record
ord-2d00104a4abc4fec961436abf759b098
Source dataset
uspto-grants-1993_11
Patent number
US05266668

Reaction notes

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