Bromine → HCID 178470329, compound

HRID 648575Notes

Reaction equation

HRID 648575 reaction equation
[Br:1]Br.[C:3]([C:6]1[S:10][C:9]([OH:11])=[N:8][C:7]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:5])[CH3:4]>C(Cl)Cl.C(O)(=O)C>[Br:1][CH2:4][C:3]([C:6]1[S:10][C:9]([OH:11])=[N:8][C:7]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5]

Participants

5

Reactant 2

HCID 24408BromineHCID 178470328HCID 178470328, compound

Product 1

HCID 178470329HCID 178470329, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromine (10.8 g) in methylene chloride (5 ml) was dropwise added to a solution of ethyl 5-acetyl-2-hydroxy-4-thiazolecarboxylate (12.9 g) in a mixture of methylene chloride (150 ml) and acetic acid (10 ml) at 30° C. to 35° C. with stirring and the mixture was stirred at the same temperature for 30 minutes. An insoluble material was filtered off. The filtrate was washed brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was triturated with diisopropyl ether to give ethyl 5-(2-bromoacetyl)-2-hydroxy-4-thiazolecarboxylate (16.7 g). mp 105°-108° C.

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. filtrationAn insoluble material was filtered off
  3. washThe filtrate was washed brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-207f2d4a49ba4c61a10530fe70a38665
Source dataset
uspto-grants-1988_04
Patent number
US04735957

Reaction notes

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