Phenol → 2-Bromo-5-phenoxy-1,3,4-thiadiazole

HRID 878432Notes

Reaction equation

HRID 878432 reaction equation
[Br:1][C:2]1[S:3][C:4](Br)=[N:5][N:6]=1.[C:8]1([OH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.C(Cl)(Cl)Cl>[Br:1][C:2]1[S:3][C:4]([O:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][N:6]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 30925302,5-Dibromo-1,3,4-thiadiazole

Product 1

HCID 646246912-Bromo-5-phenoxy-1,3,4-thiadiazole

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,5-dibromo-1,3,4-thiadiazole (1.00 g, 4.10 mmol; prepared as described in Yasuda, T.; Imase, T.; Sasaki, S.; Yamamoto, T. Macromolecules 2005, 38, 1500) and phenol (188 mg, 2.00 mmol; Aldrich) in anhydrous tetrahydrofuran (4 mL) was treated with cesium carbonate (2.0 g, 6.0 mmol) and heated to reflux for 5 hours. The mixture was cooled to room temperature, diluted with chloroform, filtered through Celite, and the residue was purified by flash chromatography (Analogix 40×120 mm 80 g silica gel column, chloroform) to afford the title compound: 1H NMR (300 MHz, chloroform-D) δ ppm 7.28-7.35 (m, 3H), 7.41-7.49 (m, 2H). MS (+ESI) m/z=257/259 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. filtrationfiltered through Celite
  4. customthe residue was purified by flash chromatography (Analogix 40×120 mm 80 g silica gel column, chloroform)

Sources & evidence

ORD record
ord-421b756e3a184b3b9a8a75690167d47b
Source dataset
uspto-grants-2015_03
Patent number
US08987453B2

Reaction notes

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