N-bromobutanimide → (5-(Bromomethyl)-2-chlorophenoxy)(tert-butyl)dimethylsilane

HRID 1801601노트

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HRID 1801601 반응식
[C:1]([Si:5]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[Cl:16])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:17][CH2:15][C:13]1[CH:12]=[CH:11][C:10]([Cl:16])=[C:9]([CH:14]=1)[O:8][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 59803183Tert-butyl(2-chloro-5-methylphenoxy)dimethylsilane

생성물 1

HCID 59803153(5-(Bromomethyl)-2-chlorophenoxy)(tert-butyl)dimethylsilane수율 34%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 6212Chloroform용매

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온도
85 °C

실험 절차

A solution containing tert-butyl(2-chloro-5-methylphenoxy)dimethylsilane 80 (6.15 g, 24 mmol), N-bromosuccinimide (4.7 g, 26 mmol), and benzoyl peroxide (0.058 g, 0.24 mmol) in 40 mL of dry CHCl3 was purged with N2 and heated to 85° C. The reaction was exposed to a 60 W lamp and was stirred at reflux for 4 h. The lamp was removed and the reaction was cooled to room temperature. The solution was concentrated and was redissolved in ether. The mixture was filtered and then concentrated again. The crude material was purified by silica gel chromatography using a 5% to 20% gradient of EtOAc in hexanes as the eluant. The desired fractions were combined and concentrated to give (5-(bromomethyl)-2-chlorophenoxy)(tert-butyl)dimethylsilane 81 (2.7 g, 34% yield). The product was carried forth to the next step as is.

후처리

  1. customwas purged with N2
  2. temperatureat reflux for 4 h
  3. customThe lamp was removed
  4. temperaturethe reaction was cooled to room temperature
  5. concentrationThe solution was concentrated
  6. dissolutionwas redissolved in ether
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated again
  9. customThe crude material was purified by silica gel chromatography
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-660a01eeb39c4108b2878d66517f8590
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349831B2

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