Methanol → 1,3-Difluoro-2,4-dimethoxy-5-nitrobenzene

HRID 355398

반응식

HRID 355398 반응식
[Na].F[C:3]1[C:8]([F:9])=[C:7](F)[C:6]([F:11])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[CH3:15][O-:16].[Na+:17].[CH3:18][OH:19]>C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:15][O-:16].[Na+:17].[F:9][C:8]1[C:3]([O:19][CH3:18])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=[C:6]([F:11])[C:7]=1[O:16][CH3:15]

참가 물질

7

반응물 4

HCID 887MethanolHCID 796912,3,4,5-TetrafluoronitrobenzeneHCID 5360545SodiumHCID 10942334Sodium Methoxide2회

생성물 2

HCID 106564751,3-Difluoro-2,4-dimethoxy-5-nitrobenzeneHCID 10942334Sodium Methoxide

시약·촉매·용매 1

HCID 311Citric Acid촉매

실험 절차

Sodium methoxide (1.0M) is prepared by adding freshly cut sodium metal (rinsed with toluene) portionwise to anhydrous methanol (Aldrich Chemical Co.) under nitrogen in flame-dried glassware with stirring; an ice-water bath is used to control the reaction temperature. To 9.8 g (50 mmol) of 2,3,4,5-tetrafluoronitrobenzene (Aldrich) under nitrogen at room temperature in flame-dried glassware is added sodium methoxide solution (2.2 equivalents) via syringe over the course of 5-10 minutes, with stirring. The resulting reaction mixture is stirred at room temperature, while monitoring the progress of the reaction by thin layer chromatography (TLC). Additional sodium methoxide solution is added as necessary. Once the reaction reaches completion (1-24 hours), several drops of 1M citric acid are added, and the reaction mixture is partitioned between ether and water. The aqueous layer is extracted once with ether. The combined organic portions are washed once with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give Compound 1 as 10.92 g (99%) of a pale yellow solid: m.p. 32.0°-32.5° C.; 1H NMR (CDCl3) 7.52 (dd, 1H), 4.12 (s, 3H), 4.04 (s, 3H); 19F NMR (CDCl3) 132.0 (m, 1F), 141.9 (d, 1F). Anal. calc. for C8H7NO4F2 : C, 43.85; H, 3.22; N, 6.39. Found: C, 43.84; H, 3.15; N, 6.15.

후처리

  1. customan ice-water bath is used
  2. stirringwith stirring
  3. customThe resulting reaction mixture
  4. stirringis stirred at room temperature
  5. customthe progress of the reaction by thin layer chromatography (TLC)
  6. additionare added
  7. customthe reaction mixture is partitioned between ether and water
  8. extractionThe aqueous layer is extracted once with ether
  9. washThe combined organic portions are washed once with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0d863e9060e54a52aa480ef5a70046eb
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05830912

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