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

HRID 1499721
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HRID 1499721 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.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]
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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 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.

후처리

  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

출처 및 근거

ORD 기록
ord-e8510ea7f3e140e1aaafa95a34f28f58
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09199982B2

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