Trimethylsilyldiazomethane → 4-Amino-3-chloro-2-fluoro-5-nitro-benzoic acid methyl ester

HRID 217069노트

반응식

HRID 217069 반응식
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:14])[C:3]=1[Cl:15].[Si](C=[N+]=[N-])(C)(C)[CH3:17]>C1COCC1.CO>[CH3:17][O:7][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]([NH2:1])=[C:3]([Cl:15])[C:4]=1[F:14]

참가 물질

5

반응물 2

HCID 167693TrimethylsilyldiazomethaneHCID 211141824-Amino-3-chloro-2-fluoro-5-nitro-benzoic acid

생성물 1

HCID 858681944-Amino-3-chloro-2-fluoro-5-nitro-benzoic acid methyl ester수율 39.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 4-amino-3-chloro-2-fluoro-5-nitro-benzoic acid 3a (3.61 g, 15.4 mmol) in THF (30 mL) and MeOH (10 mL), TMS diazomethane (9.23 mL, 2.0 M solution in hexanes, 18.5 mmol) is added. After completion of reaction, the reaction mixture is concentrated via rotary evaporation with acetic acid in the trap. The recovered oily solid is triturated with diethyl ether to provide 1.51 g of a yellow solid. The filtrate is concentrated and triturated with diethyl ether to give an additional 0.69 g of yellow solid. A total of 2.20 g (57%) of pure desired product is recovered.

후처리

  1. customAfter completion of reaction
  2. concentrationthe reaction mixture is concentrated via rotary evaporation with acetic acid in the trap
  3. customThe recovered oily solid is triturated with diethyl ether

출처 및 근거

ORD 기록
ord-a2425dd159b845498503a9c6ac7e2d83
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193231B2

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