Ammonium Chloride → (6-Bromo-4-methylpyridin-3-yl)(2,5-difluorophenyl)methanol

HRID 1641673

反応式

HRID 1641673 の反応式
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[CH:23]=[CH:22][C:21]([F:24])=[CH:20][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[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:16]=2[F:15])[OH:19])=[C:11]([CH3:13])[CH:12]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 1376632,5-DifluorobenzaldehydeHCID 27344292,5-Dibromo-4-methylpyridineHCID 178418339Butyllithium

生成物 1

HCID 57736414(6-Bromo-4-methylpyridin-3-yl)(2,5-difluorophenyl)methanol収率 34%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

実験手順

In an argon atmosphere, a hexane solution of n-butyllithium M, 8.22 ml, 13.2 mmol) was added to a solution of 2,5-dibromo-4-methylpyridine (3.00 g, 12.0 mmol) in diethyl ether (120 ml) at −78° C. After stirring the reaction mixture for 30 minutes, 2,5-difluorobenzaldehyde (1.34 ml, 12.0 mmol) was added. After stirring for 1 hour at the same temperature, saturated aqueous ammonium chloride was added at room temperature. After the organic layer was separated, the organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. 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 (1.26 g, 4.01 mmol, 34%) as a white solid.

後処理

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

出典と根拠

ORDレコード
ord-34104e0a00724cbab9759f5380b05975
出典データセット
uspto-grants-2012_02
特許番号
US08114886B2

関連ノート

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