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

HRID 600167Notes

Reaction equation

HRID 600167 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4e1a2ee7abcf4ec094d7430d9a3aec0e
Source dataset
uspto-grants-2011_03
Patent number
US07901794B2

Reaction notes

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