Ethyl bromopyruvate → Ethyl 2-(5-bromo-2-fluoro-phenyl)thiazole-4-carboxylate

HRID 521919Notes

Reaction equation

HRID 521919 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([C:8](=[S:10])[NH2:9])[CH:7]=1.Br[CH2:13][C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([C:8]2[S:10][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 826479225-Bromo-2-fluorobenzene-1-carbothioamide

Product 1

HCID 86713863Ethyl 2-(5-bromo-2-fluoro-phenyl)thiazole-4-carboxylateYield 76.14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-2-fluoro-benzenecarbothioamide (11.8 mmol, 2840 mg) and ethyl bromopyruvate (1.05 equiv., 12.4 mmol, 1.56 mL) in ethanol (30 mL) was heated at 80° C. overnight. The mixture was concentrated and the residue was purified on silica eluted with 0 to 20% EtOAc in Heptane to afford ethyl 2-(5-bromo-2-fluoro-phenyl)thiazole-4-carboxylate (2960 mg, 76.14% Yield) as a clear oil.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified on silica
  3. washeluted with 0 to 20% EtOAc in Heptane

Sources & evidence

ORD record
ord-f2e99a77ae9a42b4ac7ce163951d8682
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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