HCID 3395423, compound → 4-(4-Thiazolyl)phenol

HRID 1030457Notes

Reaction equation

HRID 1030457 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[CH:17][S:18][CH:19]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>Br>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:16]=[CH:17][S:18][CH:19]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 3395423HCID 3395423, compound

Product 1

HCID 98153854-(4-Thiazolyl)phenolYield 63.9%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
100 °C

Procedure

To 4-(4-benzyloxyphenyl)thiazole (1.1 g) was added 47% aqueous hydrogen bromide (10ml), and the mixture was stirred at 100° C. for 30 minutes. Ice-water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated saline, dried by anhydrous sodium sulfate and then concentrated. Crystals were collected by filtration by using hexane to give 4-(4-hydroxyphenyl) thiazole (466 mg, 63.8%). The crystals were purified by recrystallization from methylene chloride-hexane. m.p. 161.5°-162° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated saline
  3. dry with materialdried by anhydrous sodium sulfate
  4. concentrationconcentrated
  5. filtrationCrystals were collected by filtration

Sources & evidence

ORD record
ord-202b7cb0ac41461ab7c4dd90063c88b6
Source dataset
uspto-grants-1992_04
Patent number
US05106732

Reaction notes

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