Toluene → 2-Phenylanthraquinone

HRID 901760

반응식

HRID 901760 반응식
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

참가 물질

8

반응물 4

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

생성물 1

HCID 3139952-Phenylanthraquinone수율 87.1%

시약·촉매·용매 3

HCID 83681Tris(1,1-dimethylethyl)phosphine촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5ccd4908694b4bceb25de6b6e78070b5
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361796B2

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