Acetic Acid → 1-Iodo-2,4-dimethyl-3-nitrobenzene

HRID 239919

반응식

HRID 239919 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N+:9]([O-:11])=[O:10].S(=O)(=O)(O)O.C(O)(=O)C.[I:21]I>O>[I:21][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[C:4]=1[CH3:8]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 807IodineHCID 1118Sulfuric AcidHCID 66722,6-Dimethylnitrobenzene

생성물 1

HCID 23248871-Iodo-2,4-dimethyl-3-nitrobenzene수율 236.9%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

To 1,3-dimethyl-2-nitro-benzene (68.5 g, 453.2 mmol) is added sulfuric acid (27.2 mL, 510 mmol), acetic acid (543.8 mL, 9.49 mol), iodine (46 g, 181.3 mmol) and HIO4 (91.9 g, 403.3 mmol). The reaction is heated to 90° C. for 7 days. The reaction mixture is cooled to ambient temperature and water (500 mL) is added. The resulting solid is collected by filtration and washed with cold water. The solid is dried under reduced pressure at 45° C. overnight to afford the title compound as a yellow solid (119 g, 95%). 1H NMR (300.16 MHz, CDCl3): δ 7.80 (d, J=8.2 Hz, 1H), 6.85 (d, J=8.2 Hz, 1H), 2.37 (s, 3H), 2.23 (s, 3H).

후처리

  1. temperatureThe reaction mixture is cooled to ambient temperature
  2. filtrationThe resulting solid is collected by filtration
  3. washwashed with cold water
  4. customThe solid is dried under reduced pressure at 45° C. overnight

출처 및 근거

ORD 기록
ord-d0b62ca0fd454239a7d154c07cd94bce
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642768B2

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