Cesium carbonate → 3-[4-(Trifluoromethyl)phenoxy]aniline

HRID 48072

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HRID 48072 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O.O>[F:17][C:16]([F:19])([F:18])[C:13]1[CH:14]=[CH:15][C:10]([O:8][C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[NH2:1])=[CH:11][CH:12]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 115683-AminophenolHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-

생성물 1

HCID 130418683-[4-(Trifluoromethyl)phenoxy]aniline수율 59%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

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온도
85 °C

실험 절차

Ex-656A) 3-Aminophenol (5.0 g, 45.8 mmol) and 4-bromo-α,α,α-trifluorotoluene (14.0 g, 62.2 mmol) were dissolved in anhydrous dimethylacetamide (20 mL), then anhydrous cesium carbonate (30 g, 92.3 mmol) and copper triflate benzene complex (200 mg) were added. The mixture was stirred and heated to 85° C. using a reflux condenser under an argon atmosphere. After 16 h, the mixture was diluted with water (120 mL), and the aqueous layer was extracted with diethyl ether (4×60 mL). The combined ether layers were washed with 3% HCl, 5% NaOH and water, then dried over anhydrous MgSO4. The ether was removed in vacuo, and the recovered oil purified by flash column chromatography on silica gel eluting with ethyl acetate in hexane (1:8) to give 6.8 g (59%) of the desired 3-(4-trifluoromethylphenoxy)aniline product as a yellow oil, which solidified to a yellow powder, 98% pure by HPLC analysis. HRMS calcd. for C13H10F3NO: 254.0792 [M+H]+, found: 254.0798.

후처리

  1. extractionthe aqueous layer was extracted with diethyl ether (4×60 mL)
  2. washThe combined ether layers were washed with 3% HCl, 5% NaOH and water
  3. dry with materialdried over anhydrous MgSO4
  4. customThe ether was removed in vacuo
  5. customthe recovered oil purified by flash column chromatography on silica gel eluting with ethyl acetate in hexane (1:8)

출처 및 근거

ORD 기록
ord-f206be651b3a4ceebb087d1bd44753d3
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699898B2

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