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

HRID 600167ノート

反応式

HRID 600167 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4e1a2ee7abcf4ec094d7430d9a3aec0e
出典データセット
uspto-grants-2011_03
特許番号
US07901794B2

反応ノート

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