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

HRID 2121943ノート

反応式

HRID 2121943 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

反応条件

温度
7.5 °C

実験手順

Added 3′-fluoroacetanilide (3.06 g, 20 mmol) cautiously to conc 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 (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. extractionextracted with EtOAc (2×100 mL)
  2. washThe combined organic layers were washed with saturated NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give the crude product (4.0 g)
  6. 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-f4cf5c5911d24217b0366192558de8d6
出典データセット
uspto-grants-2004_02
特許番号
US06696473B2

反応ノート

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