Nitric Acid → Methyl 5-chloro-2-nitrobenzeneacetate

HRID 354062

반응식

HRID 354062 반응식
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1.S(=O)(=O)(O)O.[N+:18]([O-:21])([OH:20])=[O:19]>>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:18]([O-:20])=[O:19])=[C:7]([Cl:11])[CH:6]=1.[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:6]=[C:7]([Cl:11])[CH:8]=[CH:9][C:10]=1[N+:18]([O-:21])=[O:19]

참가 물질

5

반응물 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 2733544Methyl 2-(3-chlorophenyl)acetate

생성물 2

HCID 10376538Methyl 3-chloro-4-nitrophenylacetate수율 33%HCID 13265167Methyl 5-chloro-2-nitrobenzeneacetate수율 51%

반응 조건

온도
0 °C

실험 절차

To a solution of (3-chloro-phenyl)acetic acid methyl ester (5.0 g, 27.1 mmol, commercially available) in concentrated sulfuric acid (7.5 mL, 140.7 mmol) at 0° C. was added drop-wise nitric acid (2.52 g, 70%, 28.0 mmol). After stirring at 0° C. for two hrs, the reaction mixture was poured into ice water and was extracted into dichioromethane. The organic extract was washed with brine, dried (anhydrous sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel eluting with 6% ethyl acetate in hexane to give the desired (3-chloro-4-nitro-phenyl)acetic acid methyl ester as an oil (2.1 g,33%), and (5chloro-2-nitro-phenyl)acetic acid methyl ester as an oil (3.2 g, 51%). 1H NMR (CDCl3) δ: 3.69 (s, 2H), 3.74 (s, 3H), 7.33 (dd, 1H, J=8.4 Hz, 1.9 Hz), 7.50 (d, 1H, J=1.8 Hz), 7.87 (d, 1H, J=8.4 Hz.

후처리

  1. extractionwas extracted into dichioromethane
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography over silica gel eluting with 6% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-823a3f459fa449e384e68d514017d78a
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756395B2

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