Water → 2-[(2-Nitrophenyl)sulfanyl]benzoic acid

HRID 625173

반응식

HRID 625173 반응식
[SH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].O.[OH-].[K+]>C(O)(C)C>[N+:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[S:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])([O-:20])=[O:19]

참가 물질

6

반응물 4

HCID 962WaterHCID 54432-Mercaptobenzoic AcidHCID 14797Potassium HydroxideHCID 738951-Fluoro-2-nitrobenzene

생성물 1

HCID 3769782-[(2-Nitrophenyl)sulfanyl]benzoic acid

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a solution of 2-mercapto-benzoic acid (30 g, 0.195 mol) in isopropanol (500 mL) at room temperature were added 1-fluoro-2-nitro-benzene (30.2 g, 0.214 mol), water (100 mL) and potassium hydroxide (31.1 g, 0.555 mol). The reaction mixture was stirred at room temperature overnight, quenched with water and diluted with ethyl acetate. The aqueous phase was extracted with ethyl acetate (3×400 mL) and the combined organic extracts were washed with saturated aqueous sodium chloride (500 mL), dried over magnesium sulfate, filtered, and concentrated. The crude residue was purified by flash column chromatography on silica gel to give the title compound. ESI-MS (M+1): 276 calc. for C13H9NO4S 275. 1H NMR: (CDCl3, 400 MHz): δ (ppm) 8.12-8.07 (m, 2H), 7.54-7.43 (m, 2H), 7.42-7.39 (m, 2H), 7.35-7.31 (m, 1H), 7.12-7.09 (m, 1H).

후처리

  1. customquenched with water
  2. additiondiluted with ethyl acetate
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×400 mL)
  4. washthe combined organic extracts were washed with saturated aqueous sodium chloride (500 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash column chromatography on silica gel

출처 및 근거

ORD 기록
ord-03e9cd55f6564189807a25425262894f
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09304126B2

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