Acetic Acid → 4-(5-Isopropyl-2-Methyl-1,3-Thiazol-4-Yl)-Phenol

HRID 732244Notes

Reaction equation

HRID 732244 reaction equation
[CH:1]([C:4]1[S:8][C:7]([CH3:9])=[N:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=1)([CH3:3])[CH3:2].C(O)(=O)C.Br(O)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH:1]([C:4]1[S:8][C:7]([CH3:9])=[N:6][C:5]=1[C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 24445Bromic acidHCID 578383635-Isopropyl-4-(4-Methoxy-Phenyl)-2-Methyl-1,3-Thiazole

Product 1

HCID 162024444-(5-Isopropyl-2-Methyl-1,3-Thiazol-4-Yl)-PhenolYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

While 35.8 g of 5-isopropyl-4-(4-methoxy-phenyl)-2-methyl-1,3-thiazol (5) prepared in Example 3 were added to 86 ml of acetic acid and stirred, 500 ml of 48% bromic acid were added. Subsequently, the temperature was gradually increased and stirring under reflux was continued for 18 hr. The temperature was decreased to room temperature, and 400 ml of dichloromethane were added and stirring was further continued for 30 min. Then, the dichloromethane layer was removed. Thereafter, the obtained reaction solution was added with a saturated aqueous solution of potassium carbonate to be neutralized at pH 7-8, after which the precipitated solid was filtered and then washed with water, thus obtaining 28.4 g (yield: 84%) of a title compound as a solid.

Workup

  1. temperatureSubsequently, the temperature was gradually increased
  2. stirringstirring
  3. temperatureunder reflux
  4. customwas decreased to room temperature
  5. stirringstirring
  6. waitwas further continued for 30 min
  7. customThen, the dichloromethane layer was removed
  8. customThereafter, the obtained reaction solution
  9. filtrationafter which the precipitated solid was filtered
  10. washwashed with water

Sources & evidence

ORD record
ord-99e28f6d90aa4fec9a62e66e94631da9
Source dataset
uspto-grants-2009_09
Patent number
US07585979B2

Reaction notes

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