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Ammonium Chloride → Diethyl{2-[2,3-difluoro-4-(5-fluoropyridin-2-yl)phenyl]-1,1-difluoro-2-hydroxyethyl}phosphonate

HRID 216341
ノート
印刷プレビュー

反応式

HRID 216341 の反応式
Br[C:2]([P:5](=[O:10])([O-:9])[O:6][CH2:7][CH3:8])([F:4])[F:3].[CH:11]([Mg]Cl)(C)[CH3:12].[F:16][C:17]1[C:24]([F:25])=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=2)[CH:22]=[CH:21][C:18]=1[CH:19]=[O:20].[Cl-].[NH4+]>O1CCCC1.CC(C)=O.C(Cl)Cl>[F:16][C:17]1[C:24]([F:25])=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=2)[CH:22]=[CH:21][C:18]=1[CH:19]([OH:20])[C:2]([P:5](=[O:10])([O:9][CH2:11][CH3:12])[O:6][CH2:7][CH3:8])([F:4])[F:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 86638495Ethyl bromodifluoromethylphosphonateHCID 866384972,3-Difluoro-4-(5-fluoropyridin-2-yl)benzaldehydeHCID 178418918HCID 178418918、化合物

生成物 1

HCID 86638494Diethyl{2-[2,3-difluoro-4-(5-fluoropyridin-2-yl)phenyl]-1,1-difluoro-2-hydroxyethyl}phosphonate

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
3 回
HCID 21584124Propan-2-one--dichloromethane (1/1)溶媒

反応条件

温度
-78 °C

実験手順

A solution of ethyl bromodifluoromethylphosphonate (3.2 g, 12.1 mmol) in tetrahydrofuran (20 mL) was added dropwise to a solution of isopropylmagnesium chloride (2 M in tetrahydrofuran) (6.1 mL, 12.1 mmol) in tetrahydrofuran (20 mL) at −78° C. After stirring at −78° C. for 5 min, a solution of 2,3-difluoro-4-(5-fluoropyridin-2-yl)benzaldehyde (1.92 g, 8.1 mmol) in tetrahydrofuran (20 mL) was added dropwise. After stirring for a further 5 min at −78° C. then a further 1 h between −78 and 0 then a further 1 h between 0 and ambient temperature. The reaction mixture was poured into saturated ammonium chloride and extracted with methylene chloride. Combined extracts were washed with saturated aqueous sodium bicarbonate, dried (sodium sulfate) and concentrated in vacuo to afford a slightly yellow oil. Chromatography over silica eluting with 0-40% acetone/methylene chloride afforded diethyl {2-[2,3-difluoro-4-(5-fluoropyridin-2-yl)phenyl]-1,1-difluoro-2-hydroxyethyl}phosphonate as an off-white solid.

後処理

  1. stirringAfter stirring for a further 5 min at −78° C.
  2. customa further 1 h
  3. customa further 1 h between 0 and ambient temperature
  4. extractionextracted with methylene chloride
  5. washCombined extracts were washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customto afford a slightly yellow oil

出典と根拠

ORDレコード
ord-0c6c457868c742259cdaa7875a2be4f2
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08193228B2

反応ノート

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