Iodoethane → 4-Acetyl-3-ethoxy-2-iodo-6-methylbenzonitrile

HRID 1499902Notes

Reaction equation

[C:1]([C:4]1[CH:11]=[C:10]([CH3:12])[C:7]([C:8]#[N:9])=[C:6]([I:13])[C:5]=1[OH:14])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:21](I)[CH3:22]>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:4]1[CH:11]=[C:10]([CH3:12])[C:7]([C:8]#[N:9])=[C:6]([I:13])[C:5]=1[O:14][CH2:21][CH3:22])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

The 4-acetyl-3-hydroxy-2-iodo-6-methylbenzonitrile (5.0 g, 17 mmol) was dissolved in N,N-dimethylformamide (50.0 mL) and the potassium carbonate (4.6 g, 33 mmol) and ethyl iodide (2.1 mL, 33 mmol) were added. The reaction was heated to 60° C. and monitored by LC/MS. After heating for 2 hrs the reaction was complete. This was allowed to cool, diluted with ethyl acetate (300 mL) and filtered to remove the remaining solids. The organic layer was washed with water (3×), brine, dried over magnesium sulfate and concentrated to give the crude product as a dark solid. The product was purified by FCC on silica gel eluting hexane:ethyl acetate gradient to give 4-acetyl-3-ethoxy-2-iodo-6-methylbenzonitrile as a pale yellow crystalline solid (5.0 g, 96%). LCMS calculated for C12H13INO2 (M+H)+: m/z=329.9; found: 330.0.

Workup

temperatureAfter heating for 2 hrs the reaction
temperatureto cool
filtrationfiltered
customto remove the remaining solids
washThe organic layer was washed with water (3×), brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customto give the crude product as a dark solid
customThe product was purified by FCC on silica gel
washeluting hexane

Sources & evidence

ORD record: ord-0638e4c8d86747069470eaa66da65ab6
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199982B2

Reaction notes

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