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

HRID 2121943노트

반응식

HRID 2121943 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
7.5 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f4cf5c5911d24217b0366192558de8d6
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06696473B2

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