Dimethylformamide → 1-(2-Bromooctyl)imidazole hydrobromide

HRID 2210530Notes

Reaction equation

HRID 2210530 reaction equation
[NH:1]1[CH:5]=CN=C1.[Na].[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=C.[CH3:16][N:17]([CH:19]=O)[CH3:18]>>[BrH:7].[Br:7][CH:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:16][N:17]1[CH:19]=[CH:5][N:1]=[CH:18]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 759078-Bromooct-1-eneHCID 57373095Imidazole sodium

Product 1

HCID 189218891-(2-Bromooctyl)imidazole hydrobromide

Procedure

Combine sodium imidazole (5 g) and 8-bromo-1-octene (5 g) in DMF and stir overnight. Partition the reaction product between water and dichloromethane, evaporate the organic layer and purify the resultant residue on a silica gel column. Add the imidazole compound (4.6 g) and phenol (1 g) to dichloromethane (250 ml), saturate the solution with HBr gas and stir for 4 hours. Evaporate the solvent and wash the residue with THF: hexane (1:1) to obtain 1-(2-bromooctyl)imidazole hydrobromide.

Workup

  1. customPartition the reaction product between water and dichloromethane
  2. customevaporate the organic layer
  3. custompurify the resultant residue on a silica gel column
  4. additionAdd the imidazole compound (4.6 g) and phenol (1 g) to dichloromethane (250 ml)
  5. concentrationsaturate the solution with HBr gas
  6. customEvaporate the solvent
  7. washwash the residue with THF: hexane (1:1)

Sources & evidence

ORD record
ord-3a6d84f6735c4dab9eee173d0bc87398
Source dataset
uspto-grants-1995_10
Patent number
US05459144

Reaction notes

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