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

HRID 1499721Notes

Reaction equation

HRID 1499721 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.CCOC(C)=O.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

6

Reactant 2

HCID 120274791-(3-Bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanoneHCID 178418260HCID 178418260, compound

Product 1

HCID 583685163-Acetyl-5-chloro-2-hydroxy-6-methylbenzonitrile

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 1-(3-bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone (4.85 g, 18.4 mmol) and copper cyanide (2.47 g, 27.6 mmol) in N-methylpyrrolidinone (15 mL) was heated at 200° C. for 1 h. After cooled to rt, the mixture was diluted with EtOAc and 1 N HCl. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, then brine and dried over magnesium sulfate, then concentrated to dry under reduced pressure. The residue was used directly in next step (3.7 g, 96%). LCMS calculated for C10H9ClNO2 (M+H)+: m/z=210.0; Found: 210.1.

Workup

  1. temperatureAfter cooled to rt
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialbrine and dried over magnesium sulfate
  6. concentrationconcentrated
  7. customto dry under reduced pressure

Sources & evidence

ORD record
ord-e8510ea7f3e140e1aaafa95a34f28f58
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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