Dimethylformamide → 2-Fluoro-4-(methylsulfonyl)benzonitrile

HRID 2246236노트

반응식

HRID 2246236 반응식
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][C:8]=1[F:17])(=O)=O.[CH3:20][N:21](C=O)C>C(OCC)(=O)C.[Cl-].[Na+].O.[C-]#N.[Zn+2].[C-]#N>[F:17][C:8]1[CH:9]=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=[CH:12][C:7]=1[C:20]#[N:21]

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 86006151HCID 86006151, 화합물

생성물 1

HCID 223464252-Fluoro-4-(methylsulfonyl)benzonitrile

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of the product from Step D (662 mg, 2.06 mmol) in DMF (8 mL) was added zinc cyanide (951 mg, 8.1 mmol), and the reaction was then heated at 80° C. for 12 h. The reaction mixture was diluted with ethyl acetate and poured into brine. The organic phase was separated, and the aqueous phase was extracted with two portions of ethyl acetate. The combined organic layers were washed with brine and concentrated in vacuo. Purification by flash chromatography (50:50 hexanes/ethyl acetate) afforded the desired product.

후처리

  1. customThe organic phase was separated
  2. extractionthe aqueous phase was extracted with two portions of ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (50:50 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-49e8a3743ee341ad87cf1910c6d02962
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687492B2

반응 노트

불러오는 중…