Diethyl Ether → 2-Amino-5-bromo-4-methoxybenzonitrile

HRID 249934Notes

Reaction equation

HRID 249934 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:12]Br.C(OCC)C>O1CCOCC1>[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([Br:12])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 37231282-Amino-4-methoxybenzonitrile

Product 1

HCID 574230422-Amino-5-bromo-4-methoxybenzonitrileYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-4-methoxybenzonitrile (4.47 g, 30.2 mmol) is dissolved in 70 ml of dioxane and treated at 0° C. with bromine (1.71 ml, 33.2 mmol). It is subsequently stirred at 0° C. for one hour. After addition of diethyl ether, the resulting crystals are filtered off with suction. The desired product is obtained in 81% yield (5.52 g).

Workup

  1. filtrationthe resulting crystals are filtered off with suction

Sources & evidence

ORD record
ord-64cec1ecd91043dd8cd47a3205328125
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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