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

HRID 888372노트

반응식

HRID 888372 반응식
[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]

참가 물질

5

반응물 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride2회HCID 68496903tert-Butyl 3-bromo-5-(trifluoroacetyl)benzoate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-82aafdb8fb9041f2a0eca6e6c9461a09
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247401B2

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