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

HRID 521746ノート

反応式

HRID 521746 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
23 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-7aec9d8df3b547e6b1f7ce28ff5658ed
出典データセット
uspto-grants-2016_05
特許番号
US09328127B2

反応ノート

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