Diethyl Ether → 2,6-Dichloro-4-cyanobenzenediazonium tetrafluoroborate

HRID 494371

Reaction equation

HRID 494371 reaction equation
[NH2:1][C:2]1[C:9]([Cl:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[Cl:11].[F:12][B-:13]([F:16])([F:15])[F:14].[H+].[N:18](OCCC(C)C)=O.C(OCC)C>C(#N)C>[F:12][B-:13]([F:16])([F:15])[F:14].[Cl:11][C:3]1[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[C:9]([Cl:10])[C:2]=1[N+:1]#[N:18]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8053Isoamyl NitriteHCID 28118Tetrafluoroboric acidHCID 5227064-Amino-3,5-dichlorobenzonitrile

Product 1

HCID 866096552,6-Dichloro-4-cyanobenzenediazonium tetrafluoroborateYield 62.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-amino-3,5-dichlorobenzonitrile (2.00 g, 10.63 mmol) in acetonitrile (12 ml) was added dropwise tetrafluoroboric acid (2.80 ml, 21.27 mmol). After stirring for 10 min, isoamyl nitrite (1.50 ml, 10.63 mmol) was added and the reaction mixture was cooled to 0° C. After a further 10 min, diethyl ether (50 ml) was added and the resulting precipitate was collected by filtration and dried to give the titled compound (1.9 g).

Workup

  1. waitAfter a further 10 min
  2. filtrationthe resulting precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-642f2c82542c4638be26f180b45fce07
Source dataset
uspto-grants-2009_05
Patent number
US07538134B2

Linked notes

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