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

HRID 2080356ノート

反応式

HRID 2080356 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fbd8e20c6b424698a5ea35cad2336c5f
出典データセット
uspto-grants-2011_04
特許番号
US07932271B2

反応ノート

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