Cyanogen Bromide → HCID 21459520, compound

HRID 372958Notes

Reaction equation

HRID 372958 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[NH:9][C:10]([Br:16])=[C:11]([Br:15])[C:12]=1[C:13]#[N:14].[N:17]#[C:18]Br>O1CCCC1.O>[Br:7][C:8]1[N:9]([C:18]#[N:17])[C:10]([Br:16])=[C:11]([Br:15])[C:12]=1[C:13]#[N:14]

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 10471741HCID 10471741, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21459520HCID 21459520, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium t-butoxide (614 mg, 5.74 mmol) is added in portions at room temperature to a solution of 2,4,5-tribromopyrrole-3-carbonitrile (1.50 g, 4.56 mmol) in anhydrous tetrahydrofuran (20 mL). After 15 minutes a solution of cyanogen bromide (177 mg, 5.74 mmol) in tetrahydrofuran (5 mL) is added dropwise. The reaction solution is stirred at room temperature overnight as it turns cloudy. The mixture is diluted with water and extracted with ethyl acetate. The organic layer is washed with water and saturated sodium chloride and dried over (Na2SO4). Evaporation of the solvent and crystallization of the residue from ether gives a white solid (1.20 g); mp 195.0°-197.5° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water and saturated sodium chloride
  3. dry with materialdried over (Na2SO4)
  4. customEvaporation of the solvent and crystallization of the residue from ether

Sources & evidence

ORD record
ord-7464a20a08264b57b527bb703cccd1a3
Source dataset
uspto-grants-1992_11
Patent number
US05162308

Reaction notes

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