Water → 2-(3-Iodophenoxy)-1,3-thiazole

HRID 1625052Notes

Reaction equation

HRID 1625052 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[S:9][CH:10]=[CH:11][N:12]=1.[I:13][C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1.O>CN(C=O)C>[I:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[O:20][C:8]1[S:9][CH:10]=[CH:11][N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 122723-IodophenolHCID 764302-Bromothiazole

Product 1

HCID 607538412-(3-Iodophenoxy)-1,3-thiazoleYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

Cesium carbonate (4.52 g, 13.87 mmol) was added to 2-bromo-1,3-thiazole (1.90 g, 11.6 mmol) and 3-iodophenol (2.54 g, 11.5 mmol) in anhydrous DMF (30 mL). The reaction was heated to 135° C. and stirred at this temperature overnight. The reaction was allowed to cool, then was poured into water (100 mL), and extracted with EtOAc (3×100 mL). The combined organics were washed with brine (100 mL), dried (MgSO4), filtered, and concentrated. The crude product was purified via flash chromatography using a Varian SF15-24 g column and an eluent of EtOAc in hexanes (0-10%) to afford the title compound as a yellow oil (2.52 g, 71.8%). MS (LCMS) m/z 304.1 (M+1).

Workup

  1. temperatureto cool
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organics were washed with brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified via flash chromatography

Sources & evidence

ORD record
ord-6778c37d5ca046d182169f83b1cf9415
Source dataset
uspto-grants-2014_07
Patent number
US08779148B2

Reaction notes

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