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

HRID 1641697ノート

反応式

HRID 1641697 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[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e9ca1cc13c424495b5ada26415834050
出典データセット
uspto-grants-2012_02
特許番号
US08114886B2

反応ノート

読み込み中…