Ammonium Chloride → (6-Bromo-4-methylpyridin-3-yl)(2,3,6-trifluorophenyl)methanol

HRID 1641697노트

반응식

HRID 1641697 반응식
C([Li])CCC.[Br:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10](Br)=[CH:9][N:8]=1.[F:15][C:16]1[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:17]=1[CH:18]=[O:19].[Cl-].[NH4+]>C(OCC)C.CCCCCC>[Br:6][C:7]1[N:8]=[CH:9][C:10]([CH:18]([C:17]2[C:20]([F:25])=[CH:21][CH:22]=[C:23]([F:24])[C:16]=2[F:15])[OH:19])=[C:11]([CH3:13])[CH:12]=1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 5178452,3,6-TrifluorobenzaldehydeHCID 27344292,5-Dibromo-4-methylpyridineHCID 178418339Butyllithium

생성물 1

HCID 86631150(6-Bromo-4-methylpyridin-3-yl)(2,3,6-trifluorophenyl)methanol수율 81.8%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8058Hexane용매

실험 절차

A hexane solution of n-butyllithium (1.54 M, 12.2 ml, 18.7 mmol) was added to a solution of 2,5-dibromo-4-methylpyridine (4.27 g, 17.0 mmol) in diethyl ether (200 ml) in an argon atmosphere at −78° C. After stirring the reaction mixture for 30 minutes, 2,3,6-trifluorobenzaldehyde (1.99 ml, 17.0 mmol) was added thereto. After stirring for 30 minutes at the same temperature, saturated aqueous ammonium chloride was added to the mixture at room temperature. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=4:1 was concentrated under reduced pressure to obtain the title compound (4.60 g, 13.9 mmol, 81%) as a pale yellow solid.

후처리

  1. additionwas added to the mixture at room temperature
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe fraction obtained from an elution with hexane
  6. concentrationethyl acetate=4:1 was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e9ca1cc13c424495b5ada26415834050
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114886B2

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