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

HRID 429946노트

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HRID 429946 반응식
[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]

참가 물질

6

반응물 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 5198222-Bromo-4,6-di-tert-butylphenol2회

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6344Dichloromethane용매

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온도
45 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-df490391df204e4eb0c5092b8d5f315e
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06320047B1

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