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

HRID 1878658
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HRID 1878658 반응식
[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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-5be6eb19192d48c99c1367080640100f
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08314119B2

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