Sodium Iodide → Tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane

HRID 2065746노트

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HRID 2065746 반응식
[F:1][C:2]1[C:7]([F:8])=[C:6]([CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[OH:13].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].Br[CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN1C(=O)CCC1.O>[C:29]([Si:26]([O:25][CH2:24][CH2:23][O:13][C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]([CH3:9])=[C:7]([F:8])[C:2]=1[F:1])([CH3:28])[CH3:27])([CH3:32])([CH3:31])[CH3:30]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 593779072,3-Difluoro-4-methyl-5-nitro-phenol

생성물 1

HCID 59378019Tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane수율 62%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
100 °C

실험 절차

To a solution of 2,3-difluoro-4-methyl-5-nitro-phenol (1.02 g, 5.39 mmol) in NMP (10 ml) was added cesium carbonate (2.28 g, 7.01 mmol), sodium iodide (0.807 g, 5.39 mmol) and 2-bromoethoxy tertbutyldimethylsilane (1.5 ml, 7.01 mmol). The mixture was heated at 100° C. for one hour, then cooled to room temperature. Water was added and the mixture was extracted with EtOAc. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 9:1) gave 1.16 g (62%) of tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane as a tan solid.

후처리

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification of the crude product by flash chromatography (hexanes:EtOAc 9:1)

출처 및 근거

ORD 기록
ord-14eb0a2d2b3646d48bf375058c96034b
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288552B2

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