1-(3-Bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone → 3-Acetyl-5-chloro-2-hydroxy-6-methylbenzonitrile

HRID 510818Notes

Reaction equation

Br[C:2]1[C:3]([OH:13])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].[Cu](C#N)[C:15]#[N:16]>CN1CCCC1=O.C(OCC)(=O)C.Cl>[C:10]([C:4]1[C:3]([OH:13])=[C:2]([C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=1)[C:15]#[N:16])(=[O:12])[CH3:11]

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 1-(3-bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone (4.9 g, 18 mmol) and copper cyanide (2.5 g, 28 mmol) in N-methylpyrrolidinone (15 mL) was heated at 200° C. for 1 hour. The resulting mixture was allowed to cool to room temperature and was then diluted with ethyl acetate and 1 N HCl. The organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate and concentrated to dryness under reduced pressure to give 3-Acetyl-5-chloro-2-hydroxy-6-methylbenzonitrile (3.7 g, 96%). LCMS calculated for C10H9ClNO2 (M+H)+: m/z=210.0. found: 210.1.

Workup

temperatureto cool to room temperature
customThe organic and aqueous layers were separated
extractionthe aqueous layer was extracted with ethyl acetate
washThe combined organic layers were washed with water and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-e26a8688d3334d7a81ce667f61f1c037
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096600B2

Reaction notes

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