Imidazole → [(6-Bromonaphthalen-2-yl)oxy](tert-butyl)dimethylsilane

HRID 259790

반응식

HRID 259790 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].[SiH3]Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:6]=[CH:5]2

참가 물질

6

반응물 4

HCID 795Imidazole2회HCID 271446-Bromo-2-naphthalenolHCID 28928tert-Butyldimethylsilyl chlorideHCID 61622Chlorosilane

생성물 1

HCID 13473083[(6-Bromonaphthalen-2-yl)oxy](tert-butyl)dimethylsilane수율 74.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-Bromo-2-naphthol (10 g, 44 mmol), imidazole (7.4 g, 110 mmol), and t-butyldimethylsilyl chloride (10 g, 66 mmol) were stirred in DMF (50 mL) at room temperature overnight. TLC analysis indicated incomplete reaction, so additional imidazole (0.6 g) and silyl chloride (1.3 g) were added, and stirring continued 1 day. After evaporation of DMF, the mixture was extracted with EtOAc and 5% aqueous KHSO4, dried (Na2SO4), and evaporated. The crude product was purified by silica gel chromatography, eluting with hexane, to yield a colorless solid (11 g). mp 62°-63° C. 1H NMR (300 MHz, CDCl3): 7.90 (d, 1H, J=l Hz), 7.62 (d, 1H, J=9 Hz), 7.55 (d, 1H, J=9 Hz), 7.46 (dd, 1H, J=9, 2 Hz), 7.14 (d, 1H, J=2 Hz), 7.08 (dd, 1H, J=9,2 Hz), 1.00 (s, 9H), 0.23 (s, 6H). MS(CH4): 365 (20%, M+C2H5, 1 Br isotope pattern), 337 (base, M+H, 1 Br isotope pattern).

후처리

  1. customreaction
  2. customAfter evaporation of DMF
  3. extractionthe mixture was extracted with EtOAc and 5% aqueous KHSO4
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with hexane

출처 및 근거

ORD 기록
ord-a5d80d7583b246718f86a6891c700862
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05523302

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