Chloromethyl Methyl Ether → 1-Bromo-3,5-di-tert-butyl-2-(methoxymethoxy)benzene

HRID 429946ノート

反応式

HRID 429946 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]=1[OH:16].C(N(C(C)C)CC)(C)C.[CH3:26][O:27][CH2:28]Cl>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].C(Cl)Cl>[CH3:26][O:27][CH2:28][O:16][C:3]1[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][C:6]([C:8]([CH3:9])([CH3:10])[CH3:11])=[CH:7][C:2]=1[Br:1]

参加物

6

反応物 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 5198222-Bromo-4,6-di-tert-butylphenol2 回

生成物 1

HCID 225926381-Bromo-3,5-di-tert-butyl-2-(methoxymethoxy)benzene収率 95.4%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6344Dichloromethane溶媒

反応条件

温度
45 °C

実験手順

To a solution of 2-bromo-4,6-di-t-butylphenol (Compound D 2.54 g, 8.88 mmol) and catalytic amount of Bu4NI in 20 ml of dry CH2Cl2 at 0° C. was added diisopropylethylamine (9.51 ml, 53 mmol), followed by methoxymethyl chloride (2.02 ml, 26.6 mmol). The reaction mixture was heated to 45° C. for 12 hours. The reaction mixture was then washed with 10% citric acid, then NaHCO3 (sat.), brine, and dried over MgSO4. After filtration and removal of the solvent under reduced pressure, the residue was purified by column chromatography (pure hexane) to yield the title compound (2.79 g) as a colorless oil.

後処理

  1. washThe reaction mixture was then washed with 10% citric acid
  2. dry with materialNaHCO3 (sat.), brine, and dried over MgSO4
  3. filtrationAfter filtration and removal of the solvent under reduced pressure
  4. customthe residue was purified by column chromatography (pure hexane)

出典と根拠

ORDレコード
ord-df490391df204e4eb0c5092b8d5f315e
出典データセット
uspto-grants-2001_11
特許番号
US06320047B1

反応ノート

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