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

HRID 2180458ノート

反応式

HRID 2180458 の反応式
[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]

参加物

5

反応物 3

HCID 1049PyridineHCID 24648Sulfuryl chlorideHCID 134522776-Bromo-7-methoxy-2,2-dimethyl-chroman-4-one2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4df0d9a9f0e14c12863c46c1125b3857
出典データセット
uspto-grants-2005_05
特許番号
US06887896B1

反応ノート

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