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

HRID 2279468ノート

反応式

HRID 2279468 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e2d91b5ef02c48b78a6c9e280e36b83a
出典データセット
uspto-grants-2015_09
特許番号
US09133187B2

反応ノート

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