Tetrahydrofuran → 2-Bromo-cyclopenta[def]phenanthren-4-one

HRID 254131노트

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HRID 254131 반응식
[Br:1][C:2]1[CH:15]=[C:14]2[CH2:16][C:11]3[C:12]4[C:13]2=[C:4]([CH2:5][CH2:6][C:7]=4[CH:8]=[CH:9][CH:10]=3)[CH:3]=1.CC1(C)C(C)(C)OB(C2C3C(C(C4C=CC=CC=4)=C4C=2C=CC=C4)=CC=CC=3)[O:19]1.C([O-])([O-])=O.[K+].[K+].C1COCC1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:15]=[C:14]2[C:16](=[O:19])[C:11]3[C:12]4=[C:13]2[C:4](=[CH:5][CH:6]=[C:7]4[CH:8]=[CH:9][CH:10]=3)[CH:3]=1

참가 물질

9

반응물 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 125243632-bromo-8,9-dihydro-4H-cyclopenta[def]phenanthreneHCID 592076184,4,5,5-Tetramethyl-2-(10-phenylanthracen-9-yl)-1,3,2-dioxaborolane

생성물 1

HCID 125243702-Bromo-cyclopenta[def]phenanthren-4-one

시약·촉매·용매 4

HCID 74236Tetrabutylammonium Bromide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

The compound 2 (1.0 g, 1 eq., 2.02 mmol), 4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane (0.77 g, 1 eq., 2.02 mmol), tetrakis(triphenylphosphine)palladium(0) (0.23 g, 0.1 eq., 0.2 mmol), 2M K2CO3 (1 ml, 1 eq., 2.02 mmol), and tetrabutylammoniumbromide (0.65 g, 1 eq., 2.02 mmol) were put into a 100 ml round bottom flask under an argon gas atmosphere, and THF (50 ml) and toluene (20 ml) were added thereto. The reaction mixture was refluxed at 100° C. for 16 hours. When the reaction solution turned dark brown, water was added, and the resultant solution was extracted with ethylacetate. The extracted organic phase was dried over anhydrous magnesium sulfate and filtered to remove a solvent. The residue was dissolved in a trace amount of toluene and purified on a silica gel column. The resultant solid was recrystallized from toluene and methanol to give a material 1 represented by Formula 18 (0.71 g, 52%). 1H NMR (300 MHz, CDCl3, δ): 8.11 (s, 2H), 7.98 (s, 3H), 7.81 (s, 2H), 7.75-7.10 (m, 13H), 1.93 (m, 4H), 1.21 (m, 20H), 0.87 (m, 6H), 0.65 (broad s, 4H).

후처리

  1. extractionthe resultant solution was extracted with ethylacetate
  2. dry with materialThe extracted organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customto remove a solvent
  5. dissolutionThe residue was dissolved in a trace amount of toluene
  6. custompurified on a silica gel column
  7. customThe resultant solid was recrystallized from toluene and methanol

출처 및 근거

ORD 기록
ord-c7693fbbabb24202b4000e05f77b4fe3
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875367B2

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