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

HRID 525560
ノート
印刷プレビュー

反応式

HRID 525560 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 9794Ethyl trifluoroacetateHCID 693532,5-Dibromopyridine

生成物 1

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

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b1600a8c4476417f925ea54b64a37c66
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09340564B2

反応ノート

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