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Trifluoroacetic anhydride → 2-Chloro-5-(trifluoromethyl)nicotinonitrile

HRID 2089246
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HRID 2089246 반응식
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([NH2:6])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([C:11]([F:14])([F:12])[F:13])=[CH:7][C:3]=1[C:4]#[N:6]
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참가 물질

5

반응물 3

HCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 734250142-Chloro-5-(trifluoromethyl)nicotinamide

생성물 1

HCID 200715992-Chloro-5-(trifluoromethyl)nicotinonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a solution of 2-chloro-5-(trifluoromethyl)nicotinamide (as prepared in the previous step, 788 mg, 3.51 mmol) in dry DCM was added TEA (1.1 mL, 7.89 mmol). After cooling to 0° C. under argon, trifluoroacetic anhydride (0.54 mL, 3.88 mmol) was added dropwise. After stirring for 1.5 hours at 0° C., DCM (30 mL) and saturated aqueous sodium bicarbonate were introduced. The organic layer was removed and concentrated in vacuo. The resulting residue was purified by flash chromatography (silica gel, DCM) to afford the product as a tan solid.

후처리

  1. customThe organic layer was removed
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified by flash chromatography (silica gel, DCM)

출처 및 근거

ORD 기록
ord-748b7e15e1e9435ba4bbb6c7f73524cb
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08436023B2

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