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

HRID 748736ノート

反応式

HRID 748736 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. customAfter drying the solvent
  3. customthe residue obtained by concentration under reduced pressure
  4. customwas purified by silica gel chromatography, whereby the title compound (120 mg, 9%)
  5. customwas obtained as a white solid

出典と根拠

ORDレコード
ord-68bbf5d4e96642e1b55ea642ce0f81bb
出典データセット
uspto-grants-2008_07
特許番号
US07399775B2

反応ノート

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