Imidazole → (2-Bromo-5-(trifluoromethyl)benzyloxy)(tert-butyl)dimethylsilane

HRID 2075023노트

반응식

HRID 2075023 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH2:12][OH:13].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:10])([F:11])[F:9])=[CH:4][C:3]=1[CH2:12][O:13][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 27562482-Bromo-5-(trifluoromethyl)benzyl alcohol

생성물 1

HCID 58968745(2-Bromo-5-(trifluoromethyl)benzyloxy)(tert-butyl)dimethylsilane수율 97.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (2-bromo-5-(trifluoromethyl)phenyl)methanol (from Preparation 2, 10 g, 39 mmol) in DMF (20 mL) was added imidazole (5.87 g, 86.3 mmol) followed by t-butyldimethylsilyl chloride (7.11 g, 47.2 mmol) and the reaction was stirred at room temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography over 25+M Biotage silica column (eluted with 0-20% ethyl acetate in heptane) (5CV), 20% (1 CV) to afford a colorless oil (14 g, 97%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 0.15 (s, 6H) 0.98 (s, 9H) 4.75 (s, 2H) 7.36 (m, 1H) 7.60 (d, J=8.3 Hz, 1H) 7.84 (s, 1H)). GCMS: 311 (M-57, t-bu).

후처리

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography over 25+M Biotage silica column (eluted with 0-20% ethyl acetate in heptane) (5CV), 20% (1 CV)

출처 및 근거

ORD 기록
ord-d1a4daba6f1c421d9888d925c3e03bd6
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919506B2

반응 노트

불러오는 중…