Acetic Acid → 1-(3-Fluoro-4-(methylsulfonyl)phenyl)propan-2-one

HRID 908200ノート

反応式

HRID 908200 の反応式
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[C:9]([N+]([O-])=O)[CH3:10])[CH:5]=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15].C(O)(=[O:20])C>[Fe]>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9](=[O:20])[CH3:10])[CH:5]=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15]

参加物

4

反応物 2

HCID 176Acetic Acid2 回HCID 665884842-Fluoro-1-methanesulfonyl-4-(2-nitro-propenyl)-benzene

生成物 1

HCID 573512781-(3-Fluoro-4-(methylsulfonyl)phenyl)propan-2-one

試薬・触媒・溶媒 1

HCID 23925Iron触媒

反応条件

温度
100 °C

実験手順

Freshly prepared 2-fluoro-1-methanesulfonyl-4-(2-nitro-propenyl)-benzene (Example 68b) (20 g, 77 mmol) in glacial acetic acid (150 ml) is added slowly in 15×10 ml portions to a stirred slurry of iron powder (46 g, 833 mmol) in glacial acetic acid (150 ml) at 60° C. The reaction mixture is heated at 100° C. for an additional 2 hours, allowed to cool to room temperature and poured on to ice water (600 ml). The mixture is filtered through celite to remove iron residues, washing with dichloromethane (300 ml). The organic layer is removed and the aqueous solution is extracted with more DCM (3×200 ml). The combined organic extracts are dried (MgSO4), filtered and concentrated to a red solution. The titled product crystallises from this solution on standing.

後処理

  1. temperatureto cool to room temperature
  2. filtrationThe mixture is filtered through celite
  3. customto remove iron residues
  4. washwashing with dichloromethane (300 ml)
  5. customThe organic layer is removed
  6. extractionthe aqueous solution is extracted with more DCM (3×200 ml)
  7. dry with materialThe combined organic extracts are dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated to a red solution
  10. customThe titled product crystallises from this solution on standing

出典と根拠

ORDレコード
ord-3623579ccba74c31a457b3b0071a74b2
出典データセット
uspto-grants-2011_09
特許番号
US08017608B2

反応ノート

読み込み中…