Potassium Phosphate, Tribasic → 2-(4-Hydroxyphenyl)naphthalene-1,4-dione

HRID 1958219노트

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HRID 1958219 반응식
Br[C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[OH:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[OH:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[C:3](=[O:13])[C:4]3[C:9]([C:10](=[O:12])[CH:11]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:17][CH:16]=1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 749441,4-Naphthalenedione, 2-bromo-HCID 75806TricyclohexylphosphineHCID 27343604-Hydroxyphenylboronic acid

생성물 1

HCID 117768692-(4-Hydroxyphenyl)naphthalene-1,4-dione수율 45.5%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매2회HCID 1140Toluene용매

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온도
100 °C

실험 절차

An example compound, 2-(4-hydroxy-phenyl)-[1,4]naphthoquinone was synthesized in the following way. To a mixture of 2-bromo-1,4-naphthoquinone (1.0 g, 4.22 mmol), 4-hydroxy phenyl boronic acid (640 mg, 4.64 mmol), potassium phosphate (3.135 g, 14.76 mmol), tri cyclo hexyl phosphine (118 mg, 0.422 mmol), toluene (20 mL) and water (1 mL) was added palladium acetate (47 mg, 0.21 mmol) under nitrogen. The reaction mix was heated to ˜100° C. for 3 h and then cooled to room temperature. Water was added and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water, brine, dried and concentrated to give crude product, which was purified by column chromatography, using 10% ethyl acetate in hexane to give (480 mg, 45% yield) of 2-(4-Hydroxy-phenyl)-[1,4]naphthoquinone; MS (ES) m/z, 251.03 (M+1).

후처리

  1. customAn example compound, 2-(4-hydroxy-phenyl)-[1,4]naphthoquinone was synthesized in the following way
  2. additionThe reaction mix
  3. temperaturecooled to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water, brine
  7. customdried
  8. concentrationconcentrated
  9. customto give crude product, which
  10. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-7cec4327350741d59d7ec75ce8915c4a
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410109B2

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