Pyridine → 6-Bromo-8-chloro-7-methoxy-2,2-dimethyl-chroman-4-one

HRID 2180458노트

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HRID 2180458 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][C:7]([CH3:15])([CH3:14])[CH2:6][C:5]2=[O:16].S(Cl)([Cl:20])(=O)=O.N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:20])[C:11]=1[O:12][CH3:13])[O:8][C:7]([CH3:14])([CH3:15])[CH2:6][C:5]2=[O:16]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 24648Sulfuryl chlorideHCID 134522776-Bromo-7-methoxy-2,2-dimethyl-chroman-4-one2회

생성물 1

HCID 224910326-Bromo-8-chloro-7-methoxy-2,2-dimethyl-chroman-4-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of 6-bromo-7-methoxy-2,2-dimethyl-chroman-4-one (Compound 4, 2.80 g, 9.8 mmol) in methylene chloride (50 nL) at 0° C. were added sulfuryl chloride (1.59 g, 11.7 mmol) followed by treatment with pyridine (0.87 g, 11.7 mmol). After stirring at 0° C. and slow warning room temperature over 3 h, the reaction was quenched with ice water. The resulting mixture was extracted with dichloromethane and then the combined organic layers were washed with water and brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (silica gel, 95:5 hexane/ethyl acetate) to afford the title compound as a colorless oil.

후처리

  1. customthe reaction was quenched with ice water
  2. extractionThe resulting mixture was extracted with dichloromethane
  3. washthe combined organic layers were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by flash chromatography (silica gel, 95:5 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-4df0d9a9f0e14c12863c46c1125b3857
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887896B1

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