Potassium Nitrate → 2-Nitro-5-(trifluoromethoxy)benzoic acid

HRID 1717456

반응식

HRID 1717456 반응식
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8].[N+:15]([O-])([O-:17])=[O:16].[K+]>S(=O)(=O)(O)O.CCOC(C)=O>[N+:15]([C:10]1[CH:11]=[CH:12][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:5][C:6]=1[C:7]([OH:9])=[O:8])([O-:17])=[O:16]

참가 물질

5

반응물 2

HCID 24434Potassium NitrateHCID 660963-(Trifluoromethoxy)benzoic acid

생성물 1

HCID 219046132-Nitro-5-(trifluoromethoxy)benzoic acid

시약·촉매·용매 2

HCID 1118Sulfuric Acid용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a solution of 3-trifluoromethoxybenzoic acid (49.0 g, 0.24 mol) in sulfuric acid (500 mL) at less than 0° C. (ice-MeOH bath) was added a solution of potassium nitrate (31.3 g, 0.31 mol) in sulfuric acid (200 mL) over 20 minutes. The resulting solution was stirred at 0° C. for 2 hours, then warmed to room temperature and stirred for 18 hours. The reaction was poured into ice and the resulting acidic solution was extracted with EtOAc (5×). The combined organics were washed with H2O (1×), brine (2×), H2O (1×) and brine (1×), dried (Na2SO4), filtered and concentrated in vacuo to give the crude sub-title compound (65.7 g) as a solid contaminated with HOAc. The crude sub-title compound was dissolved in EtOAc and toluene and concentrated in vacuo to give a HOAc free solid (58.4 g, 97%) that was used in the next step without further purification.

후처리

  1. temperaturewarmed to room temperature
  2. stirringstirred for 18 hours
  3. additionThe reaction was poured into ice
  4. extractionthe resulting acidic solution was extracted with EtOAc (5×)
  5. washThe combined organics were washed with H2O (1×), brine (2×), H2O (1×) and brine (1×)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude sub-title compound (65.7 g) as a solid contaminated with HOAc
  10. concentrationtoluene and concentrated in vacuo
  11. customto give a HOAc free solid (58.4 g, 97%) that
  12. customwas used in the next step without further purification

출처 및 근거

ORD 기록
ord-366a86e84b864851aafba423aef1dc68
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803954B2

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