(Trifluoromethyl)trimethylsilane → Tert-butyl 3-bromo-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzoate

HRID 888372ノート

反応式

HRID 888372 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[F:21][C:22]([Si](C)(C)C)([F:24])[F:23].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:15]([OH:20])([C:22]([F:24])([F:23])[F:21])[C:16]([F:18])([F:19])[F:17])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:9])[CH3:10])=[O:6]

参加物

5

反応物 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride2 回HCID 68496903tert-Butyl 3-bromo-5-(trifluoroacetyl)benzoate

生成物 1

HCID 86646752Tert-butyl 3-bromo-5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

tert-Butyl 3-bromo-5-(trifluoroacetyl)benzoate (1.0 g, 2.8 mmol) was dissolved in THF (28 mL) and trifluoromethyltrimethylsilane (2.0 g, 14.1 mmol) added. The mixture was cooled to 0° C. and TBAF (0.07 g, 0.28 mmol) was added dropwise. After stirring for 15 minute additional TBAF (0.74 g, 2.8 mmol) was added. The mixture was stirred for an additional 15 minutes, allowed to warm to rt and then quenched with 1N HCl, diluted with EtOAc and the layers separated. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give title compound which was used directly step C.

後処理

  1. additionwas added
  2. temperatureto warm to rt
  3. customquenched with 1N HCl
  4. additiondiluted with EtOAc
  5. customthe layers separated
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-82aafdb8fb9041f2a0eca6e6c9461a09
出典データセット
uspto-grants-2012_08
特許番号
US08247401B2

反応ノート

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