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

HRID 1192587
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HRID 1192587 반응식
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]
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참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone
용매

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온도
200 °C

실험 절차

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 hour. After cooling to room temperature, the mixture was diluted with ethyl acetate and 1 N HCl. The layers were separated and the aqeous layer was extracted with ethyl acetate. The combined organic layers were washed with water, then brine and dried over magnesium sulfate. After concentration to dryness under reduced pressure, the residue was used directly in the next step (3.7 g, 96%). LCMS calculated for C10H9ClNO2 (M+H)+: m/z=210.0; Found: 210.1.

후처리

  1. temperatureAfter cooling to room temperature
  2. customThe layers were separated
  3. extractionthe aqeous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materialbrine and dried over magnesium sulfate
  6. concentrationAfter concentration to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-be56b57f80334838ad3558dd0755118b
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08680108B2

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