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

HRID 629408ノート

反応式

HRID 629408 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4d3dc858a8384f9bb1f0238fb4487f11
出典データセット
uspto-grants-2016_04
特許番号
US09315458B2

反応ノート

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