Chloromethyl Methyl Ether → 1-Bromo-4-methoxy-2-(methoxymethoxy)benzene

HRID 521746노트

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HRID 521746 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].C([O-])([O-])=O.[K+].[K+].[CH3:17][O:18][CH2:19]Cl>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:17][O:18][CH3:19]

참가 물질

5

반응물 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 134938392-Bromo-5-methoxyphenol

생성물 1

HCID 148270371-Bromo-4-methoxy-2-(methoxymethoxy)benzene수율 92%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
23 °C

실험 절차

Protected haloorganoboronic acid 14 was synthesized by a multi-step process. To a stirred mixture of 2-bromo-5-methoxyphenol (Albert, 2002) (2.19 g, 10.8 mmol) and K2CO3 (4.46 g, 32.3 mmol) in acetone (55 mL) was added chloromethyl methyl ether (1.63 mL, 21.5 mmol). The mixture was refluxed for 3 h and then allowed to cool to 23° C. The mixture was filtered and the filtrate was concentrated in vacuo. The crude product was then purified by flash chromatography (SiO2, hexanes:EtOAc 95:5) to provide 2-bromo-5-methoxy-1-methoxymethoxybenzene as a colorless liquid (2.43 g, 92%).

후처리

  1. temperatureThe mixture was refluxed for 3 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe crude product was then purified by flash chromatography (SiO2, hexanes:EtOAc 95:5)

출처 및 근거

ORD 기록
ord-7aec9d8df3b547e6b1f7ce28ff5658ed
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328127B2

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