四氧化硫 → 2-碘-3-硝基苯甲酸甲酯

HRID 33333

反应方程式

HRID 33333 反应方程式
[I:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH:19](OC)(OC)OC>CO>[CH3:19][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[I:1]

参与物

5

反应物 3

HCID 1118四氧化硫HCID 9005原甲酸三甲酯HCID 2209662-碘-3-硝基苯甲酸

产物 1

HCID 2640932-碘-3-硝基苯甲酸甲酯

试剂、催化剂与溶剂 1

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

实验过程

2-iodo-3-nitro-benzoic acid (61 g, 208 mmol, prepared as described in Org. Syn. Coll. Vol. I, 56-58, and 125-127), sulfuric acid (40.8 g, 416 mmol), and trimethyl orthoformate (88.4 g, 833 mmol) were dissolved in 500 mL dry MeOH. The reaction was refluxed under argon for 20 h. The reaction mixture was concentrated to 100 mL then partitioned between saturated NaHCO3(aq) and CH2Cl2. The layers were separated and the aqueous layer extrated three times with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The yellow solid was crystallized from CH2Cl2/hexanes yielding 2-iodo-3-nitro-benzoic acid methyl ester, 57.8 g (90%) as a yellow solid: m.p. 64.0-64.5° C.; 1H NMR (300 MHz, CDCl3) δ 3.99 (s, 3H), 7.54 (app t, J=7.8 Hz, 1H), 7.70 (dd, J=8.1, 1.8 Hz, 1H), 7.77 (dd, J=7.8, 1.8 Hz, 1H).

后处理

  1. temperatureThe reaction was refluxed under argon for 20 h
  2. concentrationThe reaction mixture was concentrated to 100 mL
  3. customthen partitioned between saturated NaHCO3(aq) and CH2Cl2
  4. customThe layers were separated
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe yellow solid was crystallized from CH2Cl2/hexanes

来源与证据

ORD记录
ord-67c4bbd805f441dea4733673415f8456
来源数据集
uspto-grants-2008_09
专利号
US07429578B2

关联笔记

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