Water → HCID 15010187, compound

HRID 2209572Notes

Reaction equation

HRID 2209572 reaction equation
[Br:1][C:2]1[NH:6][C:5]([C:7]#[N:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.[Br:16]Br.O>O1CCOCC1>[Br:16][C:4]1[C:3]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[C:2]([Br:1])[NH:6][C:5]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 15010186HCID 15010186, compound

Product 1

HCID 15010187HCID 15010187, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A sample of 5-bromo-4-(p-chlorophenyl)pyrrole-2-carbonitrile (2.2 g., 0.0078 mol) is dissolved in 30 mL of dry dioxane. The solution is heated with bromine (1.3 g., 0.008 mol) in dioxane (20 mL) and then stirred overnight at room temperature. The reaction mixture is poured into water precipitating a tan solid (2.6 g., 92%). A portion (1.6 g) is purified by flash chromatography using 75/25 hexane/ethyl acetate to give 0.8 g of grey solid with m.p. 191°-194° C.

Workup

  1. customA portion (1.6 g) is purified by flash chromatography

Sources & evidence

ORD record
ord-7d9f22e8deda4a2d9673cd90d2974664
Source dataset
uspto-grants-1995_10
Patent number
US05455263

Reaction notes

Loading…