Methanol → Methyl 4-iodo-3-nitrobenzoate

HRID 2044208노트

반응식

HRID 2044208 반응식
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].S(=O)(=O)(O)O.[CH3:19]O>>[CH3:19][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([I:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

참가 물질

4

반응물 3

HCID 887MethanolHCID 1118Sulfuric Acid2회HCID 112085984-Iodo-3-nitrobenzoic acid3회

생성물 1

HCID 297884Methyl 4-iodo-3-nitrobenzoate수율 77%

실험 절차

The required starting material, 4-iodo-3-nitrobenzoic acid, can be prepared as described in Tetrahedron, 61, 2005, 10113-10121, or by any other suitable method. The conversion of 4-iodo-3-nitrobenzoic acid to its methyl ester using sulfuric acid and methanol is described in U.S. 2007/0135485 A1 (section [0255], page 30). The method involves reacting a methanolic solution of 4-iodo-3-nitrobenzoic acid with sulfuric acid, neutralizing the acid with sodium bicarbonate, removal of methanol, diluting with water and extracting with diethyl ether, to obtain an oily product, which was subjected to chromatography to get 4-iodo-3-nitro benzoic methyl ester as a solid in 77% yield. Diethyl ether is not a suitable solvent on an industrial scale because of its high inflammability. Also column chromatography for purification in large scale is not desirable. Hence, we have modified the reported procedure. We have found that methyl tert-butyl ether (MTBE) is a better solvent for extraction which gives the product as a solid directly without any need for chromatographic purification (98.5% HPLC) and in high yield (85%).

후처리

  1. customwith sodium bicarbonate, removal of methanol
  2. additiondiluting with water
  3. extractionextracting with diethyl ether
  4. customto obtain an oily product, which

출처 및 근거

ORD 기록
ord-355e5871fe8c4b5f81933669e4254d4b
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586792B2

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