1,2-Dibromoethane → 1-Trityl-4-(4-cyanobenzyl)imidazole

HRID 365465Notes

Reaction equation

HRID 365465 reaction equation
BrCCBr.[C:5]([C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Br)=[CH:9][CH:8]=1)#[N:6].[C:15]([N:34]1[CH:38]=[C:37](I)[N:36]=[CH:35]1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+]>C1COCC1.[Zn].C(Cl)(Cl)Cl>[C:15]([N:34]1[CH:38]=[C:37]([CH2:11][C:10]2[CH:13]=[CH:14][C:7]([C:5]#[N:6])=[CH:8][CH:9]=2)[N:36]=[CH:35]1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 78391,2-DibromoethaneHCID 25517Ammonium ChlorideHCID 869964-(Bromomethyl)benzonitrileHCID 6182524-Iodo-1-tritylimidazole

Product 1

HCID 158375331-Trityl-4-(4-cyanobenzyl)imidazole

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To an oven dried 500 ml flask was added Zn (92 mmol, 5.96 g) and then 45 mL of distilled THF via syringe. To this well stirred mixture was added 1,2-dibromoethane (9.2 mmol, 1.72 g) via pipet. This mixture was stirred at ambient temperature for 3 hr and then a solution of p-cyanobenzylbromide (59.5 mmol, 11.68 g) in THF (50 mL) was added via addition funnel over 20 minutes. The resulting mixture was stirred at ambient temperature for 6 hr. Then a mixture of 1-trityl-4-iodoimidazole (45.8 mmol, 20 g) and bis-triphenylphosphinedichloronickel (4.6 mmol, 3.0 g) was added. This was stirred at ambient temperature for 36 hr. A saturated ammonium chloride solution (125 mL) was added. Stirring was continued for 3 hr and then 1 L of chloroform was added to this mixture. The chloroform layer was drawn off, washed with dilute sodium bicarbonate then saturated sodium chloride. Dried with sodium sulfate and evaporated to a thick oil. Purified on a silica gel column eluted with chloroform to provide the title compound. 1H-NMR (CDCl3): 4.0 ppm (s, 2H); 7.1-7.6 ppm (20H); 6.6 ppm(s, 1H).

Workup

  1. customTo an oven dried 500 ml flask
  2. stirringThis mixture was stirred at ambient temperature for 3 hr
  3. stirringThe resulting mixture was stirred at ambient temperature for 6 hr
  4. additionwas added
  5. stirringThis was stirred at ambient temperature for 36 hr
  6. stirringStirring
  7. washwashed with dilute sodium bicarbonate
  8. dry with materialDried with sodium sulfate
  9. customevaporated to a thick oil
  10. customPurified on a silica gel column
  11. washeluted with chloroform

Sources & evidence

ORD record
ord-5c6078a90858424dbf099f095397479f
Source dataset
uspto-grants-2000_10
Patent number
US06127390

Reaction notes

Loading…