2-Bromopyridine → 2-[(2,5-Difluorophenyl)-hydroxymethyl]pyridine

HRID 2080356노트

반응식

HRID 2080356 반응식
CCCCCC.C([Li])CCC.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.[F:19][C:20]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=1[CH:22]=[O:23]>O.O1CCCC1>[F:19][C:20]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=1[CH:22]([OH:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

참가 물질

7

반응물 4

HCID 79732-BromopyridineHCID 8058HexaneHCID 1376632,5-DifluorobenzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 230286832-[(2,5-Difluorophenyl)-hydroxymethyl]pyridine수율 9%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A hexane solution (1.53M, 3.92 ml, 0.6 mmol) of n-butyl lithium was added dropwise to a tetrahydrofuran (10 ml) solution of 2-bromopyridine (572 μl, 6 mmol) under an argon atmosphere at −78° C., followed by stirring for 30 minutes. To the resulting brown solution was added dropwise 2,5-difluorobenzaldehyde (655 μl, 6 mmol) and the temperature of the reaction mixture was gradually raised to room temperature. To the reaction mixture was added water. The resulting mixture was then extracted with ethyl acetate. After the solvent was dried, the residue obtained by concentration under reduced pressure was purified by purification by silica gel chromatography to give the title compound (120 mg, 9%) as a white solid.

후처리

  1. extractionThe resulting mixture was then extracted with ethyl acetate
  2. customAfter the solvent was dried
  3. customthe residue obtained by concentration under reduced pressure
  4. customwas purified by purification by silica gel chromatography

출처 및 근거

ORD 기록
ord-fbd8e20c6b424698a5ea35cad2336c5f
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932271B2

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