Water → HCID 15010187, compound

HRID 1651701Notes

Reaction equation

HRID 1651701 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-8590af78c32b43e49b2baacb869c9b37
Source dataset
uspto-grants-1990_05
Patent number
US04929634

Reaction notes

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