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

HRID 459755

반응식

HRID 459755 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3b69a254da05497aae7b0e857a4bf4d4
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196085B2

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