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

HRID 1467708ノート

反応式

HRID 1467708 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-564b9f99dac14f18b4ae225e8596bbdf
出典データセット
uspto-grants-2015_04
特許番号
US08999987B2

反応ノート

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