Sodium Carbonate → 1,3-Difluoro-2,4-dimethoxybenzene

HRID 355400노트

반응식

HRID 355400 반응식
N[C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][CH3:10])=[C:4]([F:11])[C:3]=1[O:12][CH3:13].N([O-])=O.[Na+].[PH2](O)=O.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>Cl.O>[F:11][C:4]1[C:5]([O:9][CH3:10])=[C:6]([F:8])[CH:7]=[CH:2][C:3]=1[O:12][CH3:13]

참가 물질

8

반응물 5

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 4124402Phosphinic AcidHCID 106791923,5-Difluoro-2,4-dimethoxybenzenamineHCID 23668193Sodium Nitrite

생성물 1

HCID 105833621,3-Difluoro-2,4-dimethoxybenzene수율 73%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매2회

실험 절차

A 0.3M solution of Compound 2 (0.566 g, 2.99 mmol) in 4M HCl is chilled in an ice bath, and treated with a cold solution of sodium nitrite (1.05 equivalents) in water. The resulting diazonium salt solution is stirred for 15 minutes, and then hypophosphorous acid (50% aqueous solution, Aldrich, 20 equivalents) is added over 5 minutes. The resulting mixture is stirred at room temperature for two hours, then diluted with water. The resulting mixture is neutralized with aqueous sodium carbonate or sodium hydroxide, and extracted twice with ether. The organic extract is washed once with water, once with brine, and dried over anhydrous sodium sulfate. The solution is concentrated in vacuo and the resulting residue is purified by flash chromatography to give 0.38 g (73%) of Compound 3 as a clear, colorless liquid: 1H NMR (CDCl3) 6.80 (td, 1H), 6.58 (m, 1H), 4.00 (s, 3H), 3.87 (s, 3H); 19F NMR (CDCl3) 138.8 (d, 1F), 150.1 (d, 1F). Anal. calc. for C8H8O2F2 : C, 55.19; H, 4.63. Found: C, 54.76; H, 4.63.

후처리

  1. extractionextracted twice with ether
  2. extractionThe organic extract
  3. washis washed once with water, once with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe solution is concentrated in vacuo
  6. customthe resulting residue is purified by flash chromatography

출처 및 근거

ORD 기록
ord-cd18a47b02674272af664d50e6eec2d7
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05830912

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