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

HRID 1427074ノート

反応式

HRID 1427074 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 23248871-Iodo-2,4-dimethyl-3-nitrobenzene収率 236.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-80b826985258487ab1128e5dedc2b4e1
出典データセット
uspto-grants-2015_01
特許番号
US08933098B2

反応ノート

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