Methyl 2-(bromomethyl)-5-chloro-3-nitrobenzoate → 6-Chloro-4-nitroisobenzofuran-1(3H)-one

HRID 907970노트

반응식

HRID 907970 반응식
BrC[C:3]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([Cl:16])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]>O1CCOCC1.O>[Cl:16][C:10]1[CH:9]=[C:4]2[C:3]([CH2:8][O:7][C:5]2=[O:6])=[C:12]([N+:13]([O-:15])=[O:14])[CH:11]=1

참가 물질

4

반응물 1

HCID 67258857Methyl 2-(bromomethyl)-5-chloro-3-nitrobenzoate

생성물 1

HCID 672581206-Chloro-4-nitroisobenzofuran-1(3H)-one수율 82.1%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of methyl 2-(bromomethyl)-5-chloro-3-nitrobenzoate (7 g, 22.8 mmol) in 1,4-dioxane (50 mL) and water (50 mL) was heated to reflux for 4 days. Dioxane was removed under reduced pressure. The residue was extracted with EtOAc (300 mL×4). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give crude product, which was purified by silica gel chromatography (petroleum ether to petroleum ether/EtOAc=5:1) to give the title compound (4 g, yield 82%) as a white solid.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 4 days
  3. customDioxane was removed under reduced pressure
  4. extractionThe residue was extracted with EtOAc (300 mL×4)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give crude product, which
  9. customwas purified by silica gel chromatography (petroleum ether to petroleum ether/EtOAc=5:1)

출처 및 근거

ORD 기록
ord-02c9da028ee24e0e880886c909eaf48a
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012976B2

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