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Ethyl trifluoroacetate → 1-(5-Bromopyridin-2-yl)-2,2,2-trifluoroethan-1-one

HRID 1520491
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HRID 1520491 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C([O:11][C:12](=O)[C:13]([F:16])([F:15])[F:14])C>O1CCCC1.C1(C)C=CC=CC=1.[Cl-].[NH4+]>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:12](=[O:11])[C:13]([F:16])([F:15])[F:14])=[N:3][CH:4]=1
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참가 물질

6

반응물 2

HCID 9794Ethyl trifluoroacetateHCID 693532,5-Dibromopyridine

생성물 1

HCID 672952111-(5-Bromopyridin-2-yl)-2,2,2-trifluoroethan-1-one수율 68.8%

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매

실험 절차

To a stirred solution of 2,5-Dibromo-pyridine (4 g, 6.87 mmol) in dry tetrahydrofuran (30 mL) and dry toluene (40 mL) is added drop wise n-Butyl litihum (1.62 g, 25.31 mmol) at −78° C. After stirring for 15-20 minutes, added trifluoro-acetic acid ethyl ester (3.56 g, 25.31 mmol) at −78° C. then stirred at −78° C. for another 30 minutes. The reaction mixture is diluted with saturated ammonium chloride solution and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by column chromatography eluting in 20% ethyl acetate in hexane to afford the title compound (1.2 g). 1HNMR (400 MHz, DMSO-d6) δ: 7.72 (d, J=8.32 Hz, 1H), 7.85-7.88 (dd, J1=8.32 Hz, J2=2.44 Hz 1H), 8.52 (d, J=2.36 Hz, 1H). LC-MS (m/z): [M+H]=255.8.

후처리

  1. stirringthen stirred at −78° C. for another 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialOrganic layer is dried over sodium sulphate, solvent
  4. customis evaporated in vacuo
  5. custompurified by column chromatography
  6. washeluting in 20% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-75dabdebdc3b43eb8ad12249b156a4ee
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073894B2

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