Ethanol → 2-Phenylthiazole

HRID 440333Notes

Reaction equation

HRID 440333 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7]1(OB(O)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>C1(C)C=CC=CC=1>[C:7]1([C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 78412Phenyl dihydrogen orthoborate

Product 1

HCID 5474942-PhenylthiazoleYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Bromothiazole (1.2 mmol, 0.11 mL) and phenylboric acid (1.2 mmol, 0.146 g) were added to a solution of potassium carbonate (2M, 1.2 mL) and ethanol (0.6 mL) in deoxygenated toluene (12 mL). The resulting mixture was degassed for 30 minutes, then tetrakistriphenylphosphine palladium (0.036 mmol, 0.042 g) was added and the solution heated at reflux for 48 hours. The solids were removed by filtration and the solution extracted with toluene (5x), dried (MgSO4), filtered and concentrated. The residue was subjected to flash chromatography (hexane followed with 5% ethyl acetate/hexane and then 10% ethyl acetate/hexane) to afford 0.13 g (69%) of 2-phenylthiazole.

Workup

  1. customThe resulting mixture was degassed for 30 minutes
  2. temperaturethe solution heated
  3. temperatureat reflux for 48 hours
  4. customThe solids were removed by filtration
  5. extractionthe solution extracted with toluene (5x)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dd8548bddea044e2aef9314e8933d846
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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