Oxalyl chloride → 4-Chloro-3-fluoro-5-nitrobenzonitrile

HRID 1258741노트

반응식

HRID 1258741 반응식
C(Cl)(=O)C([Cl:4])=O.[F:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[C:15]=1O)[C:11]#[N:12]>CN(C=O)C>[Cl:4][C:15]1[C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[F:7]

참가 물질

4

반응물 2

HCID 65578Oxalyl chlorideHCID 679577893-Fluoro-4-hydroxy-5-nitrobenzonitrile

생성물 1

HCID 679578694-Chloro-3-fluoro-5-nitrobenzonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
-25 °C

실험 절차

Oxalyl chloride (5.44 g; 42.8 mmol) was added dropwise to a solution of 3-fluoro-4-hydroxy-5-nitrobenzonitrile (3.9 g; 21 mmol) in DMF (40 mL) at −25° C. The mixture was stirred at −25° C. for 15 min and thereafter at 80° C. for 2.5 h. The mixture was slowly poured into ice, the precipitate was filtered off and the filtrate was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was combined with the precipitate and filtered through a plug of silica gel to give the sub-title compound.

후처리

  1. waitat 80° C. for 2.5 h
  2. additionThe mixture was slowly poured into ice
  3. filtrationthe precipitate was filtered off
  4. extractionthe filtrate was extracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationfiltered through a plug of silica gel

출처 및 근거

ORD 기록
ord-b41695da678e4b95ab774655d8b84587
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466186B2

반응 노트

불러오는 중…