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

HRID 584694Notes

Reaction equation

HRID 584694 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-f4a0a9daf2ec4aa482676c635b11aa47
Source dataset
uspto-grants-2005_08
Patent number
US06927232B2

Reaction notes

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