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

HRID 1258741ノート

反応式

HRID 1258741 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
-25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b41695da678e4b95ab774655d8b84587
出典データセット
uspto-grants-2013_06
特許番号
US08466186B2

反応ノート

読み込み中…