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Stannane, tributyl(1-ethoxyethenyl)- → 1-{4-Fluoro-3-[hydroxy(phenyl)methyl]phenyl}ethanone

HRID 1365065
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HRID 1365065 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])[CH:7]=1.C([Sn](CCCC)(CCCC)[C:22]([O:24]CC)=[CH2:23])CCC>[Cl-].C([N+](CC)(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C>[F:16][C:5]1[CH:4]=[CH:3][C:2]([C:22](=[O:24])[CH3:23])=[CH:7][C:6]=1[CH:8]([OH:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
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참가 물질

6

반응물 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 54595143HCID 54595143, 화합물

생성물 1

HCID 577324311-{4-Fluoro-3-[hydroxy(phenyl)methyl]phenyl}ethanone

시약·촉매·용매 3

HCID 5946Tetraethylammonium Chloride촉매HCID 178418476HCID 178418476, 화합물촉매
HCID 6342
Acetonitrile
용매

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온도
150 °C

실험 절차

A 5 mL microwave tube was charged with (5-bromo-2-fluorophenyl)-(phenyl)methanol (1 eq), tributyl-(1-ethoxyvinyl)tin (1 eq), tetraethylammonium chloride (3 eq), bis(triphenylphosphine)palladium(II) chloride (10 mol %) and acetonitrile (3.5 mL). The reaction was heated to 150° C. for one hour using microwave irradiation. The reaction was concentrated to dryness and the residue was taken up in water and extracted with ethyl acetate. The organics were dried over magnesium sulfate, filtered and then concentrated to an oil. Purification by silica gel chromatography provided 1-{4-fluoro-3-[hydroxy(phenyl)methyl]phenyl}ethanone as an oil. H1 NMR (d6-dmso): 8.16 (dd, 1H), 7.89 (m, 1H), 7.18-7.34 (m, 6H), 6.14 (d, 1H), 5.93 (d, 1H), 2.53 (s, 3H).

후처리

  1. custommicrowave irradiation
  2. concentrationThe reaction was concentrated to dryness
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-18d3697e92a74718b348c64d4ced7a25
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07888503B2

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