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Ethyl Acetate → Tert-butyl (3-bromo-2-chloro-5-(difluoromethoxy)phenyl)(4-methoxybenzyl)carbamate

HRID 921771
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HRID 921771 반응식
[Br:1][C:2]1[C:3]([Cl:20])=[C:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:5]=[C:6]([O:8][CH:9]([F:11])[F:10])[CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:31][O:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Cl)=[CH:35][CH:34]=1.CCOC(C)=O>CN(C=O)C>[Br:1][C:2]1[C:3]([Cl:20])=[C:4]([N:12]([CH2:37][C:36]2[CH:39]=[CH:40][C:33]([O:32][CH3:31])=[CH:34][CH:35]=2)[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:5]=[C:6]([O:8][CH:9]([F:11])[F:10])[CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 699934-Methyloxybenzyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 131734933Tert-butyl (3-bromo-2-chloro-5-(difluoromethoxy)phenyl)carbamate

생성물 1

HCID 117925637Tert-butyl (3-bromo-2-chloro-5-(difluoromethoxy)phenyl)(4-methoxybenzyl)carbamate수율 72.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

tert-Butyl (3-bromo-2-chloro-5-(difluoromethoxy)phenyl)carbamate (2.78 g, 7.46 mmol) was dissolved in DMF (37.3 ml) at room temperature. NaHMDS (8.95 ml, 8.95 mmol) was added drop wise and the reaction mixture was stirred for 30 min before the addition of 4-methoxybenzyl chloride (1.321 ml, 9.70 mmol). The reaction was allowed to stir overnight. EtOAc (250 mL) was added and the organic layer was washed with 10% LiCl solution (2×, dried over Na2SO4 and concentrated. Column chromatography (120 g SiO2, 0 to 10% EtOAc-hexane gradient elution) afforded tert-butyl (3-bromo-2-chloro-5-(difluoromethoxy)phenyl)(4-methoxybenzyl)carbamate as a clear oil (2.68 g)

후처리

  1. washthe organic layer was washed with 10% LiCl solution (2×
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. washColumn chromatography (120 g SiO2, 0 to 10% EtOAc-hexane gradient elution)

출처 및 근거

ORD 기록
ord-d5b1e9ad42934526a9495766bb336644
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09273057B2

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