Dimethyl Sulfoxide → HCID 21885620, 화합물

HRID 279419노트

반응식

HRID 279419 반응식
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Cl:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.CS(C)=O.[OH-].[Na+].[CH2:22]([CH:24]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:25]Br)[CH3:23]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)C.O>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Cl:15])=[CH:9][CH:10]=3)[C:5]([CH2:5][CH:4]([CH2:12][CH3:11])[CH2:3][CH2:2][CH2:14][CH3:13])([CH2:25][CH:24]([CH2:22][CH3:23])[CH2:27][CH2:28][CH2:29][CH3:30])[C:4]=2[CH:3]=1

참가 물질

8

반응물 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 868042-Ethylhexyl bromide2회HCID 2519872,7-Dichlorofluorene2회

생성물 1

HCID 21885620HCID 21885620, 화합물수율 94%

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

To a stirred mixture of 2,7-dichlorofluorene (43 g, 0.183 mole) and 120 mL of dimethylsulfoxide (DMSO) under nitrogen is added benzyltriethylammonium chloride (2.3 g, 0.01 mole) and 60 mL of a 50 weight percent aqueous solution of sodium hydroxide. 2-Ethylhexyl bromide (85 g, 0.44 mole) is added and the mixture is agitated well for 2 hours. The reaction is exothermic, the temperature reaching 80° C. within 5 minutes after the addition of 2-ethylhexyl bromide and then falling off to 30° C. over the 2-hour reaction time. Analysis of an aliquot by high pressure liquid chromatography (HPLC) shows the complete disappearance of 2,7-dichlorofluorene and the formation of new product. Water (200 mL), and diethyl ether (250 mL) are added to the reaction mixture, stirred for 15 minutes and the layers are separated. The organic layer is washed with a saturated aqueous NaCl solution, water, dried (MgSO4) and evaporated to remove ether. Fractional vacuum distillation of the residue provides 2,7-dichloro-9,9-di(2-ethylhexyl)-fluorene as clear liquid, boiling point 200° C./1 mm Hg, (79 g, 94 percent yield); HPLC analysis shows that the product is 99 percent pure. Proton Magnetic Spectrum (PMR) analysis is consistent with the title structure.

후처리

  1. waitthe temperature reaching 80° C. within 5 minutes
  2. customfalling off to 30° C. over the 2-hour reaction time
  3. stirringstirred for 15 minutes
  4. customthe layers are separated
  5. washThe organic layer is washed with a saturated aqueous NaCl solution, water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto remove ether
  9. distillationFractional vacuum distillation of the residue

출처 및 근거

ORD 기록
ord-4f7d91a7c9224d1093e6495110dd763e
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362310B1

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