Phenol → 4-Bromo-2-phenoxy-1,3-thiazole

HRID 1527615Notes

Reaction equation

HRID 1527615 reaction equation
CN(C)C=O.Br[C:7]1[S:8][CH:9]=[C:10]([Br:12])[N:11]=1.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[Br:12][C:10]1[N:11]=[C:7]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:8][CH:9]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27632972,4-Dibromo-1,3-thiazole

Product 1

HCID 467390054-Bromo-2-phenoxy-1,3-thiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To 75 ml of N,N-dimethylformamide were added 3.00 g of 2,4-dibromothiazole, 1.74 g of phenol, and 3.44 g of potassium carbonate, and the mixture was stirred at 140° C. for 6 hours. After cooling to room temperature, 100 ml of water was added to the reaction mixture and two extractions were conducted with 100 ml of ethyl acetate. After being washed twice with 100 ml of water and once with 50 ml of saturated brine, the organic layer was dried over magnesium sulfate. After filtering the magnesium sulfate, the organic layer was concentrated and the residue was purified by column chromatography (Wakogel C-200; hexane:ethyl acetate=9:1) to give 2.86 g of an ether compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. washAfter being washed twice with 100 ml of water and once with 50 ml of saturated brine
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. filtrationAfter filtering the magnesium sulfate
  5. concentrationthe organic layer was concentrated
  6. customthe residue was purified by column chromatography (Wakogel C-200; hexane:ethyl acetate=9:1)
  7. customto give 2.86 g of an ether compound

Sources & evidence

ORD record
ord-b5f89ff85e344d42b70739d785b1624e
Source dataset
uspto-grants-2015_07
Patent number
US09089139B2

Reaction notes

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