Benzyl Bromide → HCID 70982146, compound

HRID 922599Notes

Reaction equation

HRID 922599 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].[Br:10][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1.[K+].[Br-].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[Br-:10].[CH2:24]([C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]([CH3:11])[C:21]=1[N+:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[NH:5][CH:4]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 5

HCID 7498Benzyl BromideHCID 14797Potassium Hydroxide2×HCID 703202-BromomethylnaphthaleneHCID 1400184,5-DichloroimidazoleHCID 253877Potassium Bromide

Product 1

HCID 70982146HCID 70982146, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

4,5-dichloroimidazole (10.0 mmol, 1.370 g) and KOH (11.0 mmol, 0.617 g) were placed in a 50 mL round bottom flask with 10 mL acetonitrile. The mixture was brought to reflux (85° C.) and stirred 1 h until KOH was consumed. 2-Bromomethylnapthalene (10.00 mmol, 2.211 g) was added and the solution was stirred 2.5 hours. KBr was removed by vacuum filtration and benzyl bromide (10 mmol) was added to the filtrate. The mixture was stirred at reflux for 1.5 hours. The white precipitate was collected by filtration and analyzed. 1H NMR (500 MHz, d6-DMSO): δ 5.51 (2, 2H), 5.65 (s, 2H), 7.94-8.02 (m, 8H), 7.95-8.06 (m, 4H), 9.63 (s, 1H) ppm.

Workup

  1. customwas consumed
  2. additionwas added to the filtrate
  3. stirringThe mixture was stirred
  4. temperatureat reflux for 1.5 hours
  5. filtrationThe white precipitate was collected by filtration

Sources & evidence

ORD record
ord-865dcfcb6c234fe9b8b56427e83039c5
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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