Iodine → 2-iodine-4 -(trifluoromethyl) anisole

HRID 1028636노트

반응식

HRID 1028636 반응식
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:4]=1N.N(OC(C)(C)C)=O.[I:21]I>C(Cl)Cl>[I:21][C:4]1[CH:6]=[C:7]([C:10]([F:13])([F:12])[F:11])[CH:8]=[CH:9][C:3]=1[O:2][CH3:1]

참가 물질

5

반응물 3

HCID 807IodineHCID 10906Tert-Butyl nitriteHCID 6006372-Methoxy-5-(trifluoromethyl)aniline

생성물 1

HCID 187062962-iodine-4 -(trifluoromethyl) anisole

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
70 °C

실험 절차

To a stirred solution of 2-methoxy-5-(trifluoromethyl)aniline (500 mg, 2.62 mmol) in CH2Cl2 (10 mL) was added t-butyl nitrite (467 μL, 3.93 mmol). The reaction was stirred for 5 min prior to addition of iodine (1.3 g, 5.24 mmol), and then heated at 70° C. for 2 h. The reaction was cooled, diluted with CH2Cl2 (10 mL), washed with sat. Na2S2O3 (10 mL) and brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash silica gel chromatography (hexanes) to afford 2-iodo-1-methoxy-4-(trifluoromethyl)benzene as a light yellow solid. 1H NMR (CDCl3, 500 MHz): δ 8.05 (d, J=2 Hz, 1 H), 7.61 (dd, J=8.7, 1.8 Hz, 1 H), 6.89 (d, J=8.7 Hz, 1 H), 3.97 (s, 3 H).

후처리

  1. temperatureThe reaction was cooled
  2. washwashed with sat. Na2S2O3 (10 mL) and brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash silica gel chromatography (hexanes)

출처 및 근거

ORD 기록
ord-c46a75d80afd45b0b757b068b936273c
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735435B2

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