Ammonia → 3,5-Dibromo-2-(trifluoromethyl)pyridine

HRID 2388025노트

반응식

HRID 2388025 반응식
I[C:2]1[C:7]([Br:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[F-].[K+].[F:12][C:13]([Si](C)(C)C)([F:15])[F:14].N>CN1C(=O)CCC1.[Cu]I>[Br:8][C:7]1[C:2]([C:13]([F:15])([F:14])[F:12])=[N:3][CH:4]=[C:5]([Br:9])[CH:6]=1

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 269675523,5-Dibromo-2-iodopyridine

생성물 1

HCID 110449423,5-Dibromo-2-(trifluoromethyl)pyridine수율 46.1%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 13387N-methyl-2-pyrrolidone용매

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온도
50 °C

실험 절차

To a solution of 2-iodo-3,5-dibromopyridine (4.21 g, 11.60 mmol) in NMP (25 mL) were added copper(I) iodide (4.42 g, 23.21 mmol), potassium fluoride (1.35 g, 23.21 mmol), and (trifluoromethyl)trimethylsilane (5.61 mL, 35.90 mmol). The resulting mixture was allowed to stir overnight at 50° C. The mixture was poured into 12% aqueous ammonia, and then extracted with Et2O (2×120 mL). The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3,5-dibromo-2-(trifluoromethyl)pyridine (1.63 g, 46%) as a liquid.

후처리

  1. extractionextracted with Et2O (2×120 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-96c9bdf4dd304fdc937fd480e00dd023
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268992B2

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