Thionyl Chloride → 1-(4-(chloromethyl)-3-fluorophenyl)-1H-pyrazole

HRID 629408노트

반응식

HRID 629408 반응식
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[CH2:13]O.S(Cl)([Cl:17])=O>C1COCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Cl:17][CH2:13][C:3]1[CH:4]=[CH:5][C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)=[CH:7][C:2]=1[F:1]

참가 물질

6

반응물 2

HCID 24386Thionyl ChlorideHCID 59028616(2-fluoro-4-(1H-pyrazol-1-yl)phenyl)methanol

생성물 1

HCID 590285991-(4-(chloromethyl)-3-fluorophenyl)-1H-pyrazole

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of (2-fluoro-4-(1H-pyrazol-1-yl)phenyl)methanol (0.71 g) in THF (15.0 mL) was added thionyl chloride (0.40 mL) under ice-cooling, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, saturated aqueous sodium bicarbonate was added thereto, and the mixture was partitioned. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.50 g).

후처리

  1. temperaturecooling
  2. additionwas added
  3. customthe mixture was partitioned
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-4d3dc858a8384f9bb1f0238fb4487f11
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315458B2

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