Sulfuric Acid → Methyl 2-iodo-3-nitrobenzoate

HRID 489556

반응식

HRID 489556 반응식
[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]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 9005Trimethyl orthoformateHCID 2209662-Iodo-3-nitrobenzoic acid

생성물 1

HCID 264093Methyl 2-iodo-3-nitrobenzoate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9dce9530018b4a4a984e7b17ac7b9af8
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977298B2

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