Sulfuric Acid → 1-(5-Chloro-2-nitrophenyl)ethanone

HRID 38637

반응식

HRID 38637 반응식
OS(O)(=O)=O.[N+:6]([O-:9])(O)=[O:7].OS(O)(=O)=O.[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)=[O:17]>[N+]([O-])(O)=O>[CH3:15][C:16]([C:18]1[CH:19]=[C:20]([Cl:24])[CH:21]=[CH:22][C:23]=1[N+:6]([O-:9])=[O:7])=[O:17]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 149331-(3-Chlorophenyl)ethanoneHCID 71777668Sulfuric acid, mixt. with nitric acid

생성물 1

HCID 2555821-(5-Chloro-2-nitrophenyl)ethanone수율 55.8%

시약·촉매·용매 1

HCID 944Nitric Acid용매

실험 절차

65% HNO3 (80 ml) was stirred at −5° C.±1° C. and 98% H2SO4 (10 mix 10) was added dropwise. To the stirring solution of HNO3/H2SO4 was added 3-chloroacetophenone (54) (12.0 g, 77.6 mmol). The mixture was stirred at −5□±1□ for 3 h and poured into crushed ice, and extracted with CH2Cl2. The extract was dried over MgSO4 and evaporated. The crude product was purified by column chromatography (silica gel, n-hexane/EtOAc=15:1) to give 55 as yellow solid (9.3 g, 46.6 mmol). Yield: 55.8%; mp 47-49° C.; 1H-NMR (CDCl3, 200 MHz): δ 2.48 (s, 3H), 7.32 (d, J=2.4 Hz, 1H), 7.49 (dd, J=8.8, 2.2 Hz, 1H), 8.00 (d, J=8.8 Hz, 1H); 13C-NMR (CDCl3, 50 MHz) δ: 198.27, 143.78, 141.05, 139.44, 130.55, 127.36, 125.91, 30.06; Anal. Calcd for C8H6ClNO3: C, 48.14; H, 3.03; N, 7.02.

후처리

  1. additionpoured
  2. custominto crushed ice
  3. extractionextracted with CH2Cl2
  4. dry with materialThe extract was dried over MgSO4
  5. customevaporated
  6. customThe crude product was purified by column chromatography (silica gel, n-hexane/EtOAc=15:1)

출처 및 근거

ORD 기록
ord-fb4d35d4eb8d41f68fff833a02e62f18
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524740B2

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