2-Bromo-1-(4-fluorophenyl)ethan-1-one → 4-(4-Fluorophenyl)-1,3-thiazole-2-carbaldehyde

HRID 1873763

Reaction equation

HRID 1873763 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=O)[CH2:7]Br)=[CH:4][CH:3]=1.C([O:14][CH:15](OCC)[C:16]([NH2:18])=[S:17])C>C(O)C>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[N:18]=[C:16]([CH:15]=[O:14])[S:17][CH:7]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 27947342,2-Diethoxythioacetamide

Product 1

HCID 37040054-(4-Fluorophenyl)-1,3-thiazole-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 g (23.04 mmol) of 4-fluorophenacyl bromide and 3.76 g (23.04 mmol) of 2,2-diethoxythioacetamide in 100 ml of ethanol were stirred at room temperature for 2 h. After concentration, the residue was treated with ethyl acetate and filtered. The filtrate was concentrated and the obtained residue, which consisted of the diethyl acetal of 4-(4-fluoro-phenyl)-thiazole-2-carbaldehyde, was treated with 100 ml of acetone/water and 1 ml of 2 N hydrochloric acid. After stirring at room temperature for 2 h, the reaction mixture was evaporated. Yield: 4.22 g.

Workup

  1. concentrationAfter concentration
  2. additionthe residue was treated with ethyl acetate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. additionwas treated with 100 ml of acetone/water and 1 ml of 2 N hydrochloric acid
  6. customthe reaction mixture was evaporated

Sources & evidence

ORD record
ord-4139f95737654de687d379e05b7df272
Source dataset
uspto-grants-2012_11
Patent number
US08304438B2

Linked notes

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