Phenylboronic Acid → 2-Bromo-5-phenyl-1,3,4-thiadiazole

HRID 1457293Notes

Reaction equation

HRID 1457293 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:10][C:11]1[S:12][C:13](Br)=[N:14][N:15]=1>C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1.C(O)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.C(Cl)Cl.C(OCC)(=O)C>[Br:10][C:11]1[S:12][C:13]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:14][N:15]=1

Participants

9

Reactant 2

HCID 66827Phenylboronic AcidHCID 30925302,5-Dibromo-1,3,4-thiadiazole

Product 1

HCID 131041172-Bromo-5-phenyl-1,3,4-thiadiazoleYield 38%

Reagents, catalysts & solvents 6

HCID 702EthanolCatalystHCID 962WaterCatalystHCID 1140TolueneCatalystHCID 10340Sodium CarbonateCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Phenylboronic acid (2.0 g, 16.4 mmol) and 2,5-dibromo-1,3,4-thiadiazole (4.0 g, 16.4 mmol) are refluxed for 24 hours in a mixture of sodium carbonate (15.64 g), toluene (60 ml), ethanol (30 ml) and water (30 ml) and tetrakis(triphenylphosphine)palladium(0) (10 mol %) as catalyst. Aqueous work-up and column chromatography (SiO2, CH2Cl2 /ethyl acetate 9:1) give 1.5 g (38% of theory) of 2-bromo-5-phenyl-1,3,4-thiadiazole.

Sources & evidence

ORD record
ord-87e6dd7e1b7044e49f352cc311bd2e79
Source dataset
uspto-grants-1998_12
Patent number
US05847149

Reaction notes

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