Trichloroacetonitrile → 2,4-Difluorobenzyl trichloroacetimidate

HRID 2296818

반응식

HRID 2296818 반응식
[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]

참가 물질

6

반응물 2

HCID 11011TrichloroacetonitrileHCID 918672,4-Difluorobenzyl alcohol

생성물 1

HCID 110770742,4-Difluorobenzyl trichloroacetimidate수율 92%

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 6344Dichloromethane용매HCID 14797Potassium Hydroxide용매

반응 조건

온도
-15 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-28cd121bda794ab8b9cb5eef5712f152
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06489364B2

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