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

HRID 418864ノート

反応式

HRID 418864 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

To a mixture of 2-bromo-1,4-naphthoquinone (1.0 g, 4.22 mmol), 4-hydroxyphenylboronic acid (640 mg, 4.64 mmol), potassium phosphate (3.135 g, 14.76 mmol), tricyclohexylphosphine (118 mg, 0.422 mmol), toluene (20 mL) and water (1 mL) was added palladium acetate (47 mg, 0.21 mmol) under N2. The reaction mixture was heated to 100° C. for 3 h. The reaction was cooled to rt and water was added. The mixture was extracted with EtOAc, and the combined organic extracts were washed with water and brine. The organic phase was separated, dried and concentrated to give crude product. Purification by column chromatography, using 10% EtOAc in hexane, gave 480 mg of 2-(4-hydroxy-phenyl)-[1,4]naphthoquinone (45%). MS (ES) m/z: 251.03 (M+1).

後処理

  1. temperatureThe reaction was cooled to rt
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined organic extracts were washed with water and brine
  4. customThe organic phase was separated
  5. customdried
  6. concentrationconcentrated
  7. customto give crude product
  8. customPurification by column chromatography

出典と根拠

ORDレコード
ord-25b455d12b0a476dac65c9e610b1a1e5
出典データセット
uspto-grants-2012_01
特許番号
US08093273B2

反応ノート

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