Triphenylphosphine → 1-(3-Bromo-4-{[(4-chloro-2-pyridinyl)methyl]oxy}phenyl)ethanone

HRID 63272노트

반응식

HRID 63272 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=1.[Br:10][C:11]1[CH:12]=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][C:16]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:10][C:11]1[CH:12]=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][C:16]=1[O:9][CH2:8][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 6080941-(3-Bromo-4-hydroxyphenyl)ethanoneHCID 2763167(4-Chloropyridin-2-yl)methanolHCID 5462977Diethyl azodicarboxylate

생성물 1

HCID 682019601-(3-Bromo-4-{[(4-chloro-2-pyridinyl)methyl]oxy}phenyl)ethanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of (4-chloro-2-pyridinyl)methanol (Commercial eg Aldrich) (0.2 g) in THF (5 ml) were added 1-(3-bromo-4-hydroxyphenyl)ethanone (0.3 g) and triphenylphosphine (0.547 g). This was stirred for 10 min before cooling and adding slowly DEAD (0.363 g). This was stirred for 16 h. The reaction mixture was partitioned between water and ethyl acetate. The aqueous was reextracted with ethyl acetate and the combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. This was purified through silica eluting with 0-35% ethyl acetate in hexane to give the title compound, 0.30 g

후처리

  1. temperaturebefore cooling
  2. stirringThis was stirred for 16 h
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. washthe combined organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThis was purified through silica eluting with 0-35% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-a429b1da3344417d94b8f0ecf4efed2d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447074B2

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