Water → 2-Bromo-4-(4-fluorophenyl)-1,3-thiazole

HRID 2263185Notes

Reaction equation

HRID 2263185 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][S:10][C:11]#[N:12])=[CH:4][CH:3]=1.[BrH:14].C(O)(=O)C.O>C(O)(=O)C>[Br:14][C:11]1[S:10][CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 41989922-(4-Fluorophenyl)-2-oxoethyl thiocyanateHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 389962072-Bromo-4-(4-fluorophenyl)-1,3-thiazoleYield 91.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2-(4-fluorophenyl)-2-oxoethyl thiocyanate (3.70 g, 19.0 mmol) in acetic acid (35 ml) was added a 25% hydrogen bromide/acetic acid (35 ml) solution, and the mixture was stirred at 130° C. for 2 hours and at room temperature for 2 hours. Water was poured into the reaction solution, and the mixture was extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of ethanol and water to give the desired product (4.50 g, 91.9%) as a solid.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from a mixed solvent of ethanol and water

Sources & evidence

ORD record
ord-301c5a66f5944c4cba5c25fb69182320
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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