Sodium Iodide → 2-(2-Chloro-4-methoxyphenyl)-3-oxobutanenitrile

HRID 550775

반응식

HRID 550775 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[Cl:10].[C:11]([CH2:13][C:14](=[O:16])[CH3:15])#[N:12].[Na].CC(C)([O-])C.[Na+].[I-].[Na+]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOCCOC.COCCOC>[C:11]([CH:13]([C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[Cl:10])[C:14](=[O:16])[CH3:15])#[N:12]

참가 물질

10

반응물 4

HCID 5238Sodium IodideHCID 27568631-Bromo-2-chloro-4-methoxybenzeneHCID 23676156Sodium t-butoxideHCID 7165049670807-22-6

생성물 1

HCID 221781542-(2-Chloro-4-methoxyphenyl)-3-oxobutanenitrile수율 801.9%

시약·촉매·용매 5

HCID 11776Triphenylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매HCID 8150Diglyme용매2회HCID 8857Ethyl Acetate용매

실험 절차

Under argon gas atmosphere, to a solution of 1-bromo-2-chloro-4-methoxybenzene (120 g) in a mixed diglyme (230 mL) and 1,2-dimethoxyethane (90 mL), sodium cyano acetone (62.6 g), sodium t-butoxide (114.6 g) and sodium iodide (81.2 g) were added with stirring at room temperature to obtain a suspension. By another process, under argon gas atmosphere, a mixture of diglyme (40 mL), palladium acetate (426 mg) and triphenylphosphine (1.99 g) was stirred for about 30 minutes at 110° C. to dissolve. This solution was dropped into the above suspension. The mixture was warmed to 110 to 115° C. of internal temperature and stirred for 7 hours. The reaction mixture was cooled, diluted with ethyl acetate (480 mL) and washed with an aqueous solution of sulfuric acid (concentrated sulfuric acid 101 g/water 660 mL). The organic layer was washed with 10% saturated aqueous solution of sodium chloride (360 mL) twice. Activated charcoal (3.6 g) was added to the organic layer. The mixture was stirred for 1 hour and filtered. The filtrate was washed with ethyl acetate (240 mL) to obtain a solution of 1-cyano-1-(2-chloro-4-methoxyphenyl)propan-2-on (971.7 g).

후처리

  1. customto obtain a suspension
  2. stirringwas stirred for about 30 minutes at 110° C.
  3. dissolutionto dissolve
  4. additionThis solution was dropped into the above suspension
  5. temperatureThe mixture was warmed to 110 to 115° C. of internal temperature
  6. stirringstirred for 7 hours
  7. temperatureThe reaction mixture was cooled
  8. washwashed with an aqueous solution of sulfuric acid (concentrated sulfuric acid 101 g/water 660 mL)
  9. washThe organic layer was washed with 10% saturated aqueous solution of sodium chloride (360 mL) twice
  10. additionActivated charcoal (3.6 g) was added to the organic layer
  11. stirringThe mixture was stirred for 1 hour
  12. filtrationfiltered
  13. washThe filtrate was washed with ethyl acetate (240 mL)

출처 및 근거

ORD 기록
ord-81c0bcd4bf2d48be9d8504a41b7fcc44
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947697B1

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