Water → 1-(3'-bromobiphenyl-2-yl)-1H-[1,2,4]triazole

HRID 478251Notes

Reaction equation

HRID 478251 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH:16]=[N:15][CH:14]=[N:13]1)CCC.[Br:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28](Br)[CH:27]=1.[Cl-].[Li+].O>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Br:25][C:26]1[CH:27]=[C:28]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[CH:29]=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 962WaterHCID 79271,3-DibromobenzeneHCID 433294Lithium ChlorideHCID 180013021-(2-tributylstannylphenyl)-1H-[1,2,4]triazole

Product 1

HCID 180012791-(3'-bromobiphenyl-2-yl)-1H-[1,2,4]triazole

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a degassed solution of 1-(2-tributylstannylphenyl)-1H-[1,2,4]triazole (300 mg, 0.7 mmol) in N,N-dimethylformamide (5 ml) was added 1,3-dibromobenzene (0.17 ml, 1.4 mmol), tetrakis(triphenylphosphine)palladium(0) (40 mg, 35 μmol), lithium chloride (293 mg, 6.9 mmol), then copper(I) iodide (13 mg, 69 μmol), and the mixture was heated at 80° C. for 5 h. The reaction was cooled to ambient temperature then poured into water (20 ml) and extracted with dichloromethane (3×20 ml). The combined organic phases were dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. Purification by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (0-1%), then by preparative thin-layer chromatography on silica gel using 5% methanol in dichloromethane as eluent, gave 1-(3′-bromobiphenyl-2-yl)-1H-[1,2,4]triazole as a colourless gel: m/z (ES+) 300, 302 (M++H).

Workup

  1. extractionextracted with dichloromethane (3×20 ml)
  2. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customPurification by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (0-1%)

Sources & evidence

ORD record
ord-682383c6bf5042b4ad93f3dea380ba38
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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