4-Bromo-2-fluorobenzotrifluoride → (S)-2-(tert-butyldimethylsilyloxy)-1-(2-fluoro-3-(trifluoromethyl)phenyl)propan-1-one

HRID 2279468노트

반응식

HRID 2279468 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[C:4]([F:12])[CH:3]=1.C([Li])CCC.[Si:18]([O:25][C@@H:26]([CH3:34])[C:27](N1CCCC1)=[O:28])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C1COCC1>[Si:18]([O:25][C@@H:26]([CH3:34])[C:27]([C:3]1[CH:2]=[CH:7][CH:6]=[C:5]([C:8]([F:11])([F:10])[F:9])[C:4]=1[F:12])=[O:28])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

참가 물질

5

반응물 3

HCID 27829044-Bromo-2-fluorobenzotrifluorideHCID 11807344(S)-2-(tert-butyldimethylsilyloxy)-1-(pyrrolidin-1-yl)propan-1-oneHCID 178418339Butyllithium

생성물 1

HCID 86705481(S)-2-(tert-butyldimethylsilyloxy)-1-(2-fluoro-3-(trifluoromethyl)phenyl)propan-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 4-bromo-2-fluoro-1-(trifluoromethyl)benzene (4.93 g, 20.3 mmol) in THF (50 mL) cooled to −78° C. was added slowly over 10 min butyl lithium (8.11 mL, 20.3 mmol, 2.5 M in hexanes). The reaction was transferred via cannula to a cooled solution (−78° C.) of 110 (4.35 g, 16.9 mmol) in THF (50 mL). The reaction was stirred for 10 min after all aryl lithium was added. The reaction was quenched with H2O and extracted with DCM. The organic layer was concentrated and the resulting residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (1 to 5% EtOAc) to afford impure (S)-2-(tert-butyldimethylsilyloxy)-1-(2-fluoro-3-(trifluoromethyl)phenyl)propan-1-one (112) which was used without further purification.

후처리

  1. additionwas added
  2. customThe reaction was quenched with H2O
  3. extractionextracted with DCM
  4. concentrationThe organic layer was concentrated
  5. customthe resulting residue was purified by SiO2 chromatography
  6. washeluting with an EtOAc/hexane gradient (1 to 5% EtOAc)

출처 및 근거

ORD 기록
ord-e2d91b5ef02c48b78a6c9e280e36b83a
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133187B2

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