Bromine → HCID 178470329, compound

HRID 1905994Notes

Reaction equation

HRID 1905994 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 with 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 with 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-7de7e034419843b9a56413b231e411de
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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