Benzothiazole → 6-Bromo-1-(benzothiazole-2-yl)pyrene

HRID 600167노트

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HRID 600167 반응식
[Br:1][C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[S:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[CH:20]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:16]3=[C:17]4[C:12](=[CH:11][CH:10]=[C:9]([C:20]5[S:19][C:23]6[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=6[N:21]=5)[C:8]4=[CH:7][CH:6]=2)[CH:13]=[CH:14][C:15]=13

참가 물질

7

반응물 4

HCID 7222BenzothiazoleHCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 176470Pyrene, 1,6-Dibromo-

생성물 1

HCID 866285966-Bromo-1-(benzothiazole-2-yl)pyrene수율 19.1%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
130 °C

실험 절차

A mixed solution of 5 g of 1,6-dibromopyrene, 2.1 g of benzothiazole, 5 g of cesium carbonate, 0.31 g of cuprous iodide, 0.12 g of triphenylphosphine, 57 mg of palladium acetate and 50 ml of dimethylformamide was heated while stirred under nitrogen gas stream at a temperature of 130° C. for 6 hours. The mixed solution was cooled to room temperature, thereafter filtered and washed with 10 ml of dimethylformamide and 100 ml of dichloromethane. The filtrate was washed twice with 50 ml of water, dried by magnesium sulfate and thereafter evaporated. The filtrate was purified by silica gel column chromatography and vacuum dried to thereafter obtain 1.1 g of 6-bromo-1-(benzothiazole-2-yl)pyrene.

후처리

  1. temperatureThe mixed solution was cooled to room temperature
  2. filtrationfiltered
  3. washwashed with 10 ml of dimethylformamide and 100 ml of dichloromethane
  4. washThe filtrate was washed twice with 50 ml of water
  5. dry with materialdried by magnesium sulfate
  6. customevaporated
  7. customThe filtrate was purified by silica gel column chromatography and vacuum
  8. customdried

출처 및 근거

ORD 기록
ord-4e1a2ee7abcf4ec094d7430d9a3aec0e
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07901794B2

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