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

HRID 258330

Reaction equation

HRID 258330 reaction equation
[F:1][C:2](=[CH2:6])[C:3](Cl)=[O:4].[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([Br: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]([Br:17])=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[Br:7])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15531BromoxynilHCID 27833352-Fluoroacryloyl chloride

Product 1

HCID 140081612,6-Dibromo-4-cyanophenyl alpha-fluoroacrylateYield 55.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g (0.092 mol) 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 5 minutes, to a solution of 24.8 g (0.09 mol) of 3,5-dibromo-4-hydroxybenzonitrile and 9.1 g (0.09 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. 17.5 g (55% of theory) of 2,6-dibromo-4-cyanophenyl α-fluoroacrylate were obtained, melting point 135° to 138° 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-ad66178dc3904c1b86ff0330f8ddf9e2
Source dataset
uspto-grants-1993_11
Patent number
US05266668

Linked notes

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