2,5-Dibromo-1,3,4-thiadiazole → HCID 22104437, compound

HRID 1457294Notes

Reaction equation

HRID 1457294 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Br:19][C:20]1[S:21][C:22](Br)=[N:23][N:24]=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>[Br:19][C:20]1[S:21][C:22]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:11][CH:12]=2)=[N:23][N:24]=1

Participants

9

Reactant 2

HCID 30925302,5-Dibromo-1,3,4-thiadiazoleHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 22104437HCID 22104437, compoundYield 65%

Reagents, catalysts & solvents 6

HCID 702EthanolCatalystHCID 962WaterCatalystHCID 1140TolueneCatalystHCID 10340Sodium CarbonateCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Octyloxyphenylboronic acid (5.9 g, 23.6 mmol) and 2,5-dibromo-1,3,4-thiadiazole (5.8 g, 23.6 mmol) are refluxed for 14 hours in a mixture of sodium carbonate (19.56 g), toluene (70 ml), ethanol (35 ml) and water (35 ml) and tetrakis(triphenylphosphine)palladium(0) (10 mol %) as catalyst. Aqueous work-up and column chromatography (SiO2, CH2Cl2) give 5.6 g (65% of theory) of 2-bromo-5-(4-octyloxyphenyl)-1,3,4-thiadiazole.

Sources & evidence

ORD record
ord-dcd20352d9824954aea9788e56b49db3
Source dataset
uspto-grants-1998_12
Patent number
US05847149

Reaction notes

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