Benzoyl Peroxide → Ethyl 2-(bromomethyl)-1,3-oxazole-4-carboxylate

HRID 602822Notes

Reaction equation

HRID 602822 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:11])[O:9][CH:10]=1)=[O:5])[CH3:2].[Br:12]N1C(=O)CCC1=O.C1C=CC(C(OOC(C2C=CC=CC=2)=O)=O)=CC=1>ClC(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:11][Br:12])[O:9][CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 10402496Ethyl 2-methyl-1,3-oxazole-4-carboxylate

Product 1

HCID 641223Ethyl 2-(bromomethyl)-1,3-oxazole-4-carboxylateYield 10.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 1.74 g (11 mmol) of 2-methyl-oxazole-4-carboxylic acid ethyl ester in 15 mL tetrachloromethane at RT, 2.994 g (17 mmol, 1.5 eq) N-bromosuccinimide and 50 mg (0.2 mmol, 0.02 eq) benzoyl peroxyde were added. The reaction mixture was stirred under reflux overnight. The reaction mixture was filtered, the filtrate was extracted with CH2Cl2 and Na2S2O3 solution. The combined organic phases were dried over Na2SO4, filtered and evaporated to dryness to yield 265 mg (10%) of 2-bromomethyl-oxazole-4-carboxylic acid ethyl ester as an yellow oil, MS: 235 (MH+).

Workup

  1. temperatureunder reflux overnight
  2. filtrationThe reaction mixture was filtered
  3. extractionthe filtrate was extracted with CH2Cl2 and Na2S2O3 solution
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-9767a780a17d47a59100c572aec2029c
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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