Sodium methanethiolate → 4-Methoxy-1-[2-(methylthio)ethyl]-2-nitrobenzene

HRID 1914699

반응식

HRID 1914699 반응식
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13].[CH3:15][S-:16].[Na+]>CCO>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][S:16][CH3:15])=[C:5]([N+:12]([O-:14])=[O:13])[CH:6]=1

참가 물질

4

반응물 2

HCID 4378561Sodium methanethiolateHCID 593530021-(2-Bromoethyl)-4-methoxy-2-nitrobenzene

생성물 1

HCID 593530214-Methoxy-1-[2-(methylthio)ethyl]-2-nitrobenzene수율 67%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
25.5 °C

실험 절차

A suspension of 1-(2-bromoethyl)-4-methoxy-2-nitrobenzene (14.7 g, 0.06 mol) in EtOH (150 mL) is stirred at 25-26° C. under a nitrogen atmosphere. Sodium thiomethoxide (7.9 g, 0.1 mol) is added in one portion at 25-26° C. and the reaction mixture is heated to reflux for 12 h. The solvent is removed under reduced pressure and the brown residue is taken up in cold water (100 mL). The crude product is extracted with EtOAc (2×200 mL). The organic layer is washed with water and brine (200 mL, each), then dried over Na2SO4 and the solvent is removed under reduced pressure to afford a brown oil. The crude product is purified by column chromatography (60-120 mesh silica gel, eluent 2% EtaAc in petrol ether) to give 8.3 g (67%) of the title compound as light brown liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.47-7.45 (m, 2H), 7.20-724(m 1H,), 3.81 (s, 3H), 3.01-2.97 (m, 2H), 2.69-2.66 (m, 2H), 2.05 (s, 3H). LC/MS: (ES+) 227.9.

후처리

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 12 h
  3. customThe solvent is removed under reduced pressure
  4. extractionThe crude product is extracted with EtOAc (2×200 mL)
  5. washThe organic layer is washed with water and brine (200 mL
  6. dry with materialeach), then dried over Na2SO4
  7. customthe solvent is removed under reduced pressure
  8. customto afford a brown oil
  9. customThe crude product is purified by column chromatography (60-120 mesh silica gel, eluent 2% EtaAc in petrol ether)

출처 및 근거

ORD 기록
ord-0561b52d6756460d813ca35781699c94
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614215B2

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