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

HRID 238293Notes

Reaction equation

HRID 238293 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.C([O:14][CH:15](OCC)[C:16]([NH2:18])=[S:17])C>C(O)C>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:18]=[C:16]([CH:15]=[O:14])[S:17][CH:2]=2)=[CH:6][CH:7]=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-carbaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 g (23.04 mmol) of 2-bromo-1-(4-fluorophenyl)-ethanone und 3.76 g (23.04 mmol) of 2,2-diethoxythioacetamide were stirred in 100 ml of ethanol at room temperature for 2 h. After concentrating, the residue was heated with ethyl acetate, the insolubles were filtered off, and the filtrate was evaporated. The obtained acetal (6.2 g) was stirred with 50 ml of acetone, 50 ml of water and 1 ml of 2N hydrochloric acid at room temperature for 4 h. Evaporation of the mixture yielded 4.22 g (88%) of the title compound.

Workup

  1. concentrationAfter concentrating
  2. temperaturethe residue was heated with ethyl acetate
  3. filtrationthe insolubles were filtered off
  4. customthe filtrate was evaporated
  5. customEvaporation of the mixture

Sources & evidence

ORD record
ord-89559df7d5644845a06a6c655fce407c
Source dataset
uspto-grants-2014_02
Patent number
US08642620B2

Reaction notes

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