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

HRID 1958219ノート

反応式

HRID 1958219 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7cec4327350741d59d7ec75ce8915c4a
出典データセット
uspto-grants-2013_04
特許番号
US08410109B2

反応ノート

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