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

HRID 593380노트

반응식

HRID 593380 반응식
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]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 79732-BromopyridineHCID 27833242-Fluoro-5-(trifluoromethoxy)benzaldehydeHCID 178418365HCID 178418365, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ff42c90ccea043e58fd1574e4d789b05
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242959B2

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