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

HRID 2065746ノート

反応式

HRID 2065746 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-14eb0a2d2b3646d48bf375058c96034b
出典データセット
uspto-grants-2012_10
特許番号
US08288552B2

反応ノート

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