Carbon Dioxide → 4-Bromo-1,3-thiazole-2-carboxylic acid

HRID 2170913Notes

Reaction equation

HRID 2170913 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:7])[N:6]=1.[Li]CCCC.[C:13](=[O:15])=[O:14]>CCOCC>[Br:7][C:5]1[N:6]=[C:2]([C:13]([OH:15])=[O:14])[S:3][CH:4]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 27632972,4-Dibromo-1,3-thiazoleHCID 178418339Butyllithium

Product 1

HCID 151220654-Bromo-1,3-thiazole-2-carboxylic acidYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the solution of 2,4-dibromothiazole (50 g, 207 mmol, 1.0 eq.) in Et2O (1000 ml) was added n-BuLi (90 ml, 2.5 M, 1.1 eq.) at −78° C. dropwise and it was stirred for one hour. The reaction solution was poured into dry CO2 at −78° C. and the reaction mixture was warmed to the room temperature. TLC and LCMS showed the reaction was complete. It was quenched with water (100 ml). The Et2O phase was removed. The aqueous phase was adjusted to pH to 2-3 and extracted with ethyl acetate. The organic phase was dried, filtered and concentrated to obtain 35 g (82% y) of the 4-bromothiazole-2-carboxylic acid.

Workup

  1. customIt was quenched with water (100 ml)
  2. customThe Et2O phase was removed
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d40f9334b7104cbc8964ce126b1067a6
Source dataset
uspto-grants-2015_06
Patent number
US09051313B2

Reaction notes

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