Bromine → 5-(2-bromo-3,5-dimethyl-3H-imidazol-4-yl)-3-methyl-[1,2,4]oxadiazole

HRID 48946Notes

Reaction equation

HRID 48946 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[O:11][N:10]=[C:9]([CH3:12])[N:8]=2)=[C:5]([CH3:13])[N:4]=[CH:3]1.[Br:14]Br>C(Cl)(Cl)Cl>[Br:14][C:3]1[N:2]([CH3:1])[C:6]([C:7]2[O:11][N:10]=[C:9]([CH3:12])[N:8]=2)=[C:5]([CH3:13])[N:4]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 222717005-(3,5-Dimethyl-3H-imidazol-4-yl)-3-methyl-[1,2,4]oxadiazole

Product 1

HCID 222717145-(2-bromo-3,5-dimethyl-3H-imidazol-4-yl)-3-methyl-[1,2,4]oxadiazoleYield 51.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 5-(3,5-dimethyl-3H-imidazol-4-yl)-3-methyl-[1,2,4]oxadiazol (0.7 g, 3.93 mmol) in chloroform (7 ml) was added dropwise at RT a solution of bromine (0.94 g, 0.30 ml, 5.89 mmol) in chloroform (7 ml). The reaction mixture was stirred at RT for 26 h, evaporated, poured into sat. NaHCO3 solution (40 ml) and extracted with dichloromethane (2×30 ml). The combined organic layers were washed with brine (40 ml), dried (MgSO4) and evaporated to give the crude product as yellow oil (0.84 g). Purification by column chromatography on silica gel (ethyl acetate/MeOH 98:2) gave the title compound (0.52 g, 51%) as a white solid, m.p. 89° C. and MS: m/e=256, 258 (M+).

Workup

  1. customevaporated
  2. additionpoured into sat. NaHCO3 solution (40 ml)
  3. extractionextracted with dichloromethane (2×30 ml)
  4. washThe combined organic layers were washed with brine (40 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give the crude product as yellow oil (0.84 g)
  8. customPurification by column chromatography on silica gel (ethyl acetate/MeOH 98:2)

Sources & evidence

ORD record
ord-ddc8445ac18840af8276d334b04eaa11
Source dataset
uspto-grants-2004_03
Patent number
US06706707B2

Reaction notes

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