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

HRID 2427292Notes

Reaction equation

HRID 2427292 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-8bb5945b16e040d197852f24c96d7b3d
Source dataset
uspto-grants-2011_06
Patent number
US07968584B2

Reaction notes

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