Isopropanol → 2-Iodo-5-(trifluoromethyl)benzoic acid

HRID 505267

반응식

HRID 505267 반응식
[OH-:1].[K+].[I:3][C:4]1C=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:5]=1C#N.[CH:16]([OH:19])([CH3:18])C>O>[I:3][C:4]1[CH:5]=[CH:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:18]=1[C:16]([OH:19])=[O:1]

참가 물질

5

반응물 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 533636442-Iodo-5-(trifluoromethyl)benzonitrile2회

생성물 1

HCID 184515332-Iodo-5-(trifluoromethyl)benzoic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Potassium hydroxide (3.78 g; 0.0673 mol) was added to a stirred solution of 2-iodo-5-(trifluoromethyl)benzonitrile (Intermediate 8; 4 g; 0.0135 mol) in a 1:1 isopropanol:H2O solution (60 mL). The reaction was heated at reflux for 14 h and then partitioned between H2O (50 mL) and EtOAc (50 mL). The aqueous layer was extracted with EtOAc (50 mL) and acidified to pH 5 with 6N HCl. The aqueous layer was further extracted with EtOAc (4×50 mL) and the combined extracts were washed with brine (50 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford 2-iodo-5-(trifluoromethyl)benzoic acid as a yellow solid. LCMS=317.0 (M+1)+. 1H NMR (CDCl3, 500 MHz): δ 8.27 (d, J=1.6 Hz, 1 H), 8.25 (d, J=8.2 Hz, 1 H), 7.47 (dd, J=8.2, 1.8 Hz, 1 H).

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 14 h
  3. custompartitioned between H2O (50 mL) and EtOAc (50 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (50 mL)
  5. extractionThe aqueous layer was further extracted with EtOAc (4×50 mL)
  6. washthe combined extracts were washed with brine (50 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a5c951da34ef4277bbd1f79587c3a502
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781426B2

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