tert-Butyl methyl ether → 4-(tert-Butyl)-3,5-difluorophenol

HRID 1438390ノート

反応式

HRID 1438390 の反応式
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.CO[C:12]([CH3:15])([CH3:14])[CH3:13]>[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-]>[C:12]([C:7]1[C:2]([F:1])=[CH:3][C:4]([OH:9])=[CH:5][C:6]=1[F:8])([CH3:15])([CH3:14])[CH3:13]

参加物

4

反応物 2

HCID 15413tert-Butyl methyl ether3 回HCID 759283,5-Difluorophenol

生成物 1

HCID 670464324-(tert-Butyl)-3,5-difluorophenol収率 54.2%

試薬・触媒・溶媒 1

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-触媒

反応条件

温度
55 °C

実験手順

A mixture of 3,5-difluorophenol (TCl, 14 g, 107 mmol), tert-butyl methyl ether (12.8 ml, 108 mmol) and zirconium(IV) chloride (25 g, 107 mmol) was stirred for 12 hours at 55 ° C., followed by addition of tert-butyl methyl ether (6.4 ml, 54 mmol). The additional injection of tert-butyl methyl ether (6.4 ml, 54 mmol), was repeated 8 times at intervals of 24 hours and then the reaction was quenched with saturated ammonium chloride aqueous solution and 2 M HCl aqueous solution. The whole was extracted with DCM, washed with brine, and dried over magnesium sulfate. The organic layer was evaporated to give a crude residue which was purified by silica gel column chromatography, eluting with gradually from hexane only to hexane/EtOAc (10:1), to give the title compound (10.8 g, 54%) as white solids.

後処理

  1. customat intervals of 24 hours
  2. customthe reaction was quenched with saturated ammonium chloride aqueous solution and 2 M HCl aqueous solution
  3. extractionThe whole was extracted with DCM
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe organic layer was evaporated
  7. customto give a crude residue which
  8. customwas purified by silica gel column chromatography
  9. washeluting with gradually from hexane only to hexane/EtOAc (10:1)

出典と根拠

ORDレコード
ord-3a7f23e3750f47fc8fdc1d1031370d93
出典データセット
uspto-grants-2009_11
特許番号
US07622589B2

反応ノート

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