Toluene → 2-Phenylanthraquinone

HRID 1827620

反応式

HRID 1827620 の反応式
Cl[C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F-].[K+].C1(C)C=CC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:18]1([C:2]2[CH:15]=[CH:14][C:13]3[C:12](=[O:16])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5](=[O:17])[C:4]=3[CH:3]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

8

反応物 4

HCID 1140TolueneHCID 85532-ChloroanthraquinoneHCID 66827Phenylboronic AcidHCID 522689Potassium Fluoride

生成物 1

HCID 3139952-Phenylanthraquinone収率 87.1%

試薬・触媒・溶媒 3

HCID 83681Tris(1,1-dimethylethyl)phosphine触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

Under an atmosphere of argon, 2-chloroanthraquinone (5.0 g, 21 mmole), phenylboronic acid (2.8 g, 23 mmole, 1.1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.2 g, 0.22 mmole, 2% Pd) and potassium fluoride (4.4 g, 76 mmole, 3.3 eq) were suspended in anhydrous dioxane (30 ml). To the obtained suspension, a toluene solution of tri-t-butylphosphine (66%, 0.13 ml, 0.42 mmole, 1 eq) was added and the resultant mixture was stirred at 80° C. for 3 hours. The reaction mixture was filtered and washed with toluene (100 ml). The filtrate was washed with a saturated aqueous solution of sodium chloride (30 ml) and dried with magnesium sulfate. Then, the solvent was removed by distillation and a yellow solid was obtained. The obtained solid was washed with boiling ethanol (50 ml) and a yellow solid (5.2 g, 87%) was obtained. 1H-NMR (CDCl3, TMS) δ: 7.4 to 7.6 (3H, m), 7.6 to 7.9 (4H, m), 7.98 (1H, dd, J=8 Hz, 2 Hz), 8.2 to 8.4 (3H, m), 8.50 (1H, d, J=2 Hz)

後処理

  1. filtrationThe reaction mixture was filtered
  2. washwashed with toluene (100 ml)
  3. washThe filtrate was washed with a saturated aqueous solution of sodium chloride (30 ml)
  4. dry with materialdried with magnesium sulfate
  5. customThen, the solvent was removed by distillation
  6. customa yellow solid was obtained
  7. washThe obtained solid was washed with boiling ethanol (50 ml)

出典と根拠

ORDレコード
ord-e777ef001ce44e7bb3ddd378ce85e87f
出典データセット
uspto-grants-2006_05
特許番号
US07053255B2

関連ノート

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