Trichloroacetonitrile → 2,4-Difluorobenzyl trichloroacetimidate

HRID 1596803ノート

反応式

HRID 1596803 の反応式
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[Cl:11][C:12]([Cl:16])([Cl:15])[C:13]#[N:14]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.[OH-].[K+]>[Cl:11][C:12]([Cl:16])([Cl:15])[C:13](=[NH:14])[O:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:2]=1[F:1]

参加物

6

反応物 2

HCID 11011TrichloroacetonitrileHCID 918672,4-Difluorobenzyl alcohol

生成物 1

HCID 110770742,4-Difluorobenzyl trichloroacetimidate収率 92%

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 6344Dichloromethane溶媒HCID 14797Potassium Hydroxide溶媒

反応条件

温度
-15 °C

実験手順

A Tetrabutyl ammonium hydrogen sulphate (15 mg) was added to 2,4-difluorobenzylalcohol (1.0 g, 6.94 mmol) in CH2Cl2 (10 ml) and KOH (50%, 10 ml). This mixture was cooled to −15° C. prior to the addition of trichloroacetonitrile (1.2 ml, 8.32 mmol). After 30 min at −15° C. and 3 h at ambient temperature the phases were separated. The aqueous phase was extracted twice with CH2Cl2. The combined organic phases were dried with MgSO4 and reduced to one third. The residue was filtered through celite and concentrated to give the crude 2,4-difluorobenzyl trichloroacetimidate (1.83 g, 92%) as a yellow oil.

後処理

  1. custom3 h at ambient temperature the phases were separated
  2. extractionThe aqueous phase was extracted twice with CH2Cl2
  3. dry with materialThe combined organic phases were dried with MgSO4
  4. filtrationThe residue was filtered through celite and
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-f9d45d4a92b04cba80d3a3d7ca7aa396
出典データセット
uspto-grants-2001_09
特許番号
US06291687B1

反応ノート

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