Water → 4-Acetyl-6-chloro-3-ethoxy-2-iodobenzonitrile

HRID 1499859Notes

Reaction equation

[Cl:1][C:2]1[C:3](F)=[C:4]([I:14])[C:5]([O:11][CH2:12][CH3:13])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[C-:16]#[N:17].[K+].C(=O)(O)[O-].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[C:8]([C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([C:16]#[N:17])=[C:4]([I:14])[C:5]=1[O:11][CH2:12][CH3:13])(=[O:10])[CH3:9]

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 1-(5-chloro-2-ethoxy-4-fluoro-3-iodophenyl)ethanone (7.3 g, 21 mmol) in N,N-dimethylformamide (80 mL)was treated with potassium cyanide (2.1 g, 32 mmol) and stirred at 40° C. for 5 h. The reaction mixture was diluted with ethyl acetate and poured into saturated sodium bicarbonate solution/water (1:1). The organic layer was separated, washed with saturated sodium bicarbonate solution, dried with magnesium sulfate, filtered, and concentrated to give a crude brown oil. The crude material was purified by flash column chromatography using ethyl acetate in hexanes (0%-30%) to give the desired product (6.1 g, 81%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.57 (s, 1H), 3.93 (q, J=7.0 Hz, 2H), 2.61 (s, 3H), 1.47 (t, J=7.0 Hz, 3H). LCMS for C11H10ClINO2 (M+H)+: m/z=349.9; Found: 349.9.

Workup

customThe organic layer was separated
washwashed with saturated sodium bicarbonate solution
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationconcentrated
customto give a crude brown oil
customThe crude material was purified by flash column chromatography

Sources & evidence

ORD record: ord-015e2ba089754eea9814b8036a771db4
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199982B2

Reaction notes

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