Triethylamine → 3-(4-fluoro-3-nitrobenzylidene)-3H-isobenzofuran-1-one

HRID 459755

反応式

HRID 459755 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4](P(=O)(OC)OC)[O:3]1.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27].C(N(CC)CC)C>O1CCCC1>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2](=[O:1])[O:3]2)=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 5981294-Fluoro-3-nitrobenzaldehydeHCID 11118213Dimethyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phosphonate

生成物 1

HCID 686245893-(4-fluoro-3-nitrobenzylidene)-3H-isobenzofuran-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A stirred solution of dimethyl 3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonate (20 g, 0.083 mol) and 4-fluoro-3-nitrobenzaldehyde (13.97 g, 0.083 mol) in tetrahydrofuran (120 ml) was cooled to 15° C. and triethylamine (11.5 ml, 0.083 mol) was added dropwise at <25° C. The mixture thickened at this point, so further tetrahydrofuran (50 ml) was added to aid stirring. The mixture was stirred at ambient temperature for 65 hours and the resulting solid was collected by filtration. The filtrate was concentrated in vacuo, the residue was triturated with water (30 ml) and the resulting solid was collected by filtration. The two crops of solid were combined and suspended in water (120 ml). The mixture was stirred at ambient temperature for 30 minutes and the resulting solid was collected by filtration and dried in vacuo for 24 hours to give crude 3-(4-fluoro-3-nitrobenzylidene)-3H-isobenzofuran-1-one, still slightly wet with water, which was used directly in the next stage.

後処理

  1. additionwas added to aid
  2. stirringThe mixture was stirred at ambient temperature for 65 hours
  3. filtrationthe resulting solid was collected by filtration
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was triturated with water (30 ml)
  6. filtrationthe resulting solid was collected by filtration
  7. stirringThe mixture was stirred at ambient temperature for 30 minutes
  8. filtrationthe resulting solid was collected by filtration
  9. customdried in vacuo for 24 hours

出典と根拠

ORDレコード
ord-3b69a254da05497aae7b0e857a4bf4d4
出典データセット
uspto-grants-2007_03
特許番号
US07196085B2

関連ノート

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