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

HRID 258330

反応式

HRID 258330 の反応式
[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]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 15531BromoxynilHCID 27833352-Fluoroacryloyl chloride

生成物 1

HCID 140081612,6-Dibromo-4-cyanophenyl alpha-fluoroacrylate収率 55.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ad66178dc3904c1b86ff0330f8ddf9e2
出典データセット
uspto-grants-1993_11
特許番号
US05266668

関連ノート

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