Toluene → 2-Phenylanthraquinone

HRID 901760

反応式

HRID 901760 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(dibenzylidene-acetone)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.

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-5ccd4908694b4bceb25de6b6e78070b5
出典データセット
uspto-grants-2008_04
特許番号
US07361796B2

関連ノート

読み込み中…