Hydrochloric Acid → (2-Fluoro-5-trifluoromethoxyphenyl)pyridin-2-ylmethanol

HRID 593380ノート

反応式

HRID 593380 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Mg]Br)(C)C.[F:13][C:14]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][C:15]=1[CH:16]=[O:17].Cl>O1CCCC1.O>[F:13][C:14]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:25])([F:26])[F:24])=[CH:18][C:15]=1[CH:16]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[OH:17]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 79732-BromopyridineHCID 27833242-Fluoro-5-(trifluoromethoxy)benzaldehydeHCID 178418365HCID 178418365、化合物

生成物 1

HCID 86703870(2-Fluoro-5-trifluoromethoxyphenyl)pyridin-2-ylmethanol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 2-bromopyridine (380 mg) in anhydrous tetrahydrofuran (3 mL) is slowly added a 1M solution of isopropylmagnesium bromide in tetrahydrofuran (2.64 mL) at room temperature. After stirring for 2 hours, 2-fluoro-5-(trifluoromethoxy)benzaldehyde (0.50 mL) is added and the reaction mixture stirred for 2 hours. After hydrolysis with water and 3N hydrochloric acid, the mixture is washed with diethyl ether, basified with concentrated sodium hydroxide and extracted with ethyl acetate twice. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (heptane/ethyl acetate 2/1) to afford (2-fluoro-5-trifluoromethoxyphenyl)pyridin-2-ylmethanol as an orange oil.

後処理

  1. stirringthe reaction mixture stirred for 2 hours
  2. washthe mixture is washed with diethyl ether
  3. extractionextracted with ethyl acetate twice
  4. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography over silica gel (heptane/ethyl acetate 2/1)

出典と根拠

ORDレコード
ord-ff42c90ccea043e58fd1574e4d789b05
出典データセット
uspto-grants-2016_01
特許番号
US09242959B2

反応ノート

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