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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
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HRID 216341 반응식
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]
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참가 물질

7

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

생성물 1

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

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
3회
HCID 21584124Propan-2-one--dichloromethane (1/1)용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0c6c457868c742259cdaa7875a2be4f2
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08193228B2

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