2,4,5-Tribromoimidazole → 1-(4-Bromobutoxymethyl)-2,4,5-tribromoimidazole

HRID 1789342Notes

Reaction equation

HRID 1789342 reaction equation
[Na].[Br:2][C:3]1[NH:4][C:5]([Br:9])=[C:6]([Br:8])[N:7]=1.[H-].[Na+].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18]Br>CN(C)C=O.O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][N:4]1[C:5]([Br:9])=[C:6]([Br:8])[N:7]=[C:3]1[Br:2]

Participants

7

Reactant 4

HCID 162532,4,5-TribromoimidazoleHCID 24758Sodium hydrideHCID 3146311-Bromo-4-(bromomethoxy)butaneHCID 5360545Sodium

Product 1

HCID 139222111-(4-Bromobutoxymethyl)-2,4,5-tribromoimidazoleYield 39.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of a sodium salt, prepared from 1.22 g of 2,4,5-tribromoimidazole and 0.16 g of 60% oil-based sodium hydride, in 5 ml of N,N-dimethylformamide was added dropwise 1.23 g of 4-bromobutoxymethyl bromide at room temperature. After stirring at room temperature for 3 hours, 50 ml of water was added to the reaction mixture which was then extracted with three 30-ml portions of ether. The ether layer was dried over magnesium sulfate and concentrated. The oily product obtained was purified by column chromatography on silica gel to obtain 0.74 g of 1-(4-bromobutoxymethyl)-2,4,5-tribromoimidazole.

Workup

  1. extractionwas then extracted with three 30-ml portions of ether
  2. dry with materialThe ether layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe oily product obtained
  5. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d34625343e7649b5af49a1270004d653
Source dataset
uspto-grants-1987_08
Patent number
US04689340

Reaction notes

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