Water → 2-Iodo-6-nitrobenzonitrile

HRID 471599Notes

Reaction equation

N[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[C:4]#[N:5].N([O-])=O.[Na+].[I-:17].[K+].O>OS(O)(=O)=O.C(O)(=O)C>[I:17][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[C:4]#[N:5]

Participants

Conditions

Temperature: 45 °C

Procedure

2-Amino-6-nitrobenzonitrile (Example 130e) (4.32 g, 26.5 mmol) was added in small portions to a suspension of sodium nitrite (2.19 g, 31.7 mmol) in concentrated H2SO4 (43 mL) and acetic acid (43 mL) at 45° C. The reaction was heated at 45° C. for 1 h and then added in small portions to a solution of potassium iodide (7.47 g, 45.0 mmol) in H2SO4 (1 M, 43 mL). After stirring at room temperature for 1.5 h, iced water was added to the reaction and the precipitated product was collected by filtration. The product was purified by chromatography on silica gel eluting with CH2Cl2, to give 2-iodo-6-nitrobenzonitrile (3.86 g, 53%) as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ 8.46-8.52 (m, 1H), 8.34-8.38 (m, 1H), 7.66-7.71 (m, 1H).

Workup

filtrationthe precipitated product was collected by filtration
customThe product was purified by chromatography on silica gel eluting with CH2Cl2

Sources & evidence

ORD record: ord-f6993b24176940b6961d30d7901e21a7
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633186B2

Reaction notes

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