Nitric Acid → N-(3-Fluoro-4-nitrophenyl)acetamide

HRID 1241972ノート

反応式

HRID 1241972 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[NH:5][C:6](=[O:8])[CH3:7].S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18].C(Cl)Cl>O>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:17]([O-:19])=[O:18])[NH:5][C:6](=[O:8])[CH3:7]

参加物

6

反応物 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 9594N-(3-Fluorophenyl)acetamide

生成物 1

HCID 2755770N-(3-Fluoro-4-nitrophenyl)acetamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Added 3′-fluoroacetanilide (3.06 g, 20 mmol) cautiously to concentrated sulfuric acid (6 mL) at 5° C. To the resulting solution, added fuming nitric acid (1.05 mL, 25 mmol) dropwise while maintaining temperature at 5–10° C. After 30 min, added ice (50 g), later diluted with water (100 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were washed with saturated NaHCO3 and brine, dried over anhydrous Na2SO4 and concentrated to give the crude product (4.0 g) as a mixture of isomers (1:1.4 ratio of 4′-nitro/2′-nitro). The desired isomer, 3′-flouro-4′-nitroacetanilide, was isolated by flash chromatography (DCM-5% MeOH/DCM) in low yield (1.2 g, 30%) as a yellow solid. 1H-NMR (CDCl3): δ 8.08 (1H, app t), 7.82 (1H, dd), 7.41 (1H, br s), 7.21 (1H, m), 2.25 (3H, s).

後処理

  1. temperaturewhile maintaining temperature at 5–10° C
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with saturated NaHCO3 and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product (4.0 g)
  7. additionas a mixture of isomers (1:1.4 ratio of 4′-nitro/2′-nitro)

出典と根拠

ORDレコード
ord-da3f4300b22e40adad5520d73a6d10ec
出典データセット
uspto-grants-2006_10
特許番号
US07115640B2

反応ノート

読み込み中…