1,10-Phenanthroline → 4,4'-Dibromo-N,N-diphenyl[1,1'-biphenyl]-2-amine

HRID 11745

반응식

HRID 11745 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[C:4]([NH2:15])[CH:3]=1.I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[K+].N1[C:38]2[C:29](=[CH:30][CH:31]=[C:32]3[C:37]=2N=CC=C3)C=CC=1>C1(C)C=CC=CC=1.[Cu]Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([Br:14])=[CH:12][CH:13]=2)=[C:4]([N:15]([C:29]2[CH:38]=[CH:37][CH:32]=[CH:31][CH:30]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:3]=1

참가 물질

7

반응물 4

HCID 13181,10-PhenanthrolineHCID 11575IodobenzeneHCID 14797Potassium HydroxideHCID 45594205-Bromo-2-(4-bromophenyl)aniline

생성물 1

HCID 219763174,4'-Dibromo-N,N-diphenyl[1,1'-biphenyl]-2-amine수율 835.7%

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 1140Toluene용매2회

실험 절차

4,4′-Dibromo-2-amino-1,1′-biphenyl (16.35 g, prepared according to Libman and Slack (1951) J. Chem. Soc., p. 2588), iodobenzene (26.52 g, 0.13 mol), flake potassium hydroxide (22.4 g, 0.35 mol), 1,10-phenanthroline (0.45 g), copper (I) chloride (0.25 g), and toluene (30 ml) were charged into a flask and stirred at reflux for 15 hours. The dark reaction mixture was cooled to room temperature and diluted with 200 ml of toluene. The toluene solution was washed with DI water, dried with magnesium sulfate, and evaporated. The dark residue obtained was recrystallized trice from hexane/toluene (4:1 volume) to yield 10 grams of white crystals to yield the desired monomer. 1H NMR (CDCl3): δ=6.8–7.5, multiple peaks.

후처리

  1. temperatureat reflux for 15 hours
  2. customThe dark reaction mixture
  3. washThe toluene solution was washed with DI water
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. customThe dark residue obtained
  7. customwas recrystallized trice from hexane/toluene (4:1 volume)

출처 및 근거

ORD 기록
ord-709f53a743134d82ad7ff2bb00604b97
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098297B2

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