1,2-Dibromoethane → 3,3'',5,5''-Tetra-naphthyl-p-quaterphenyl

HRID 47178

반응식

HRID 47178 반응식
[C:1]1([C:11]2[CH:12]=[C:13](Br)[CH:14]=[C:15]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)[CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Mg].Br[CH2:30][CH2:31]Br.I[C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43](I)=[CH:42][CH:41]=2)=[CH:36][CH:35]=1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]1([C:11]2[CH:12]=[C:13]([C:34]3[CH:39]=[CH:38][C:37]([C:40]4[CH:45]=[C:44]([C:4]5[C:5]6[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=6)[CH:1]=[CH:2][CH:3]=5)[C:43]([C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=5)=[C:42]([C:20]5[C:30]6[C:31](=[CH:19][CH:18]=[CH:17][CH:26]=6)[CH:23]=[CH:22][CH:21]=5)[CH:41]=4)=[CH:36][CH:35]=3)[CH:14]=[C:15]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)[CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 78391,2-DibromoethaneHCID 763484,4'-Diiodo-1,1'-biphenylHCID 5462224MagnesiumHCID 227436841,1'-(5-Bromo-1,3-phenylene)dinaphthalene

생성물 1

HCID 227436863,3'',5,5''-Tetra-naphthyl-p-quaterphenyl수율 81%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매4회

반응 조건

온도
60 °C

실험 절차

A solution of 3,5-di-α-naphthyl bromobenzene (10.0 g, 0.0244 mol) in anhydrous THF (70 mL) was added dropwise to magnesium turnings (0.59 g, 0.0244 mol) in 10 mL THF. The solution was heated at 60° C. during the addition and the reaction was initiated using 1,2-dibromoethane. After the addition was complete, the brown solution was heated at reflux for 2 hrs. and then cooled to room temperature. In a separate flask, 4,4′-diiodobiphenyl (3.3 g 0.008 mol) and 0.3 g of dichlorobis(triphenyl phosphine)palladium(II) were placed under nitrogen and 30 mL of anhydrous THF was added. The Grignard reagent prepared about THF solution was then added using needle-transfer and an orange solution resulted. Heat was applied and the solution turned to almost black. The mixture was then heated at reflux for 45 min. and cooled to room temperature during which time a solid precipitated out of solution. A 2.0 M solution of HCl was added to the mixture and after stirring for 30 minutes, the water layer was removed. The solid precipitate was collected by filtration and washed with water and diethyl ether to yield a white solid (5.3 g, 81%)

후처리

  1. additionAfter the addition
  2. temperaturethe brown solution was heated
  3. temperatureat reflux for 2 hrs
  4. temperatureand then cooled to room temperature
  5. additionwas then added
  6. customan orange solution resulted
  7. temperatureHeat
  8. temperatureThe mixture was then heated
  9. temperatureat reflux for 45 min.
  10. temperaturecooled to room temperature during which time a solid
  11. customprecipitated out of solution
  12. additionA 2.0 M solution of HCl was added to the mixture
  13. customthe water layer was removed
  14. filtrationThe solid precipitate was collected by filtration
  15. washwashed with water and diethyl ether

출처 및 근거

ORD 기록
ord-12c65c39c56a4a428c86722dd8dd49d5
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699595B2

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