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Methanol → 2-Bromo-1-(benzyloxymethyl)-3,5-bis(methoxymethoxy)benzene

HRID 505660
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HRID 505660 반응식
[Br:1][C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=1[CH2:16][OH:17].[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CO>CN(C)C=O.O>[Br:1][C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=1[CH2:16][O:17][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
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참가 물질

7

반응물 4

HCID 887MethanolHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10957768[2-Bromo-3,5-bis(methoxymethoxy)phenyl]methanol

생성물 1

HCID 231475942-Bromo-1-(benzyloxymethyl)-3,5-bis(methoxymethoxy)benzene수율 73.2%

시약·촉매·용매 2

HCID 962Water
용매
HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

The above-obtained [2-bromo-3,5-bis(methoxymethoxy)phenyl]methanol (3.5 g, 11 mmol) was dissolved in N,N-dimethylformamide (20 mL) and cooled to 0° C. The obtained solution was added with 60% sodium hydride-oil dispersion (0.59 g, 15 mmol) and benzyl bromide (2.0 mL, 17 mmol), followed by stirring at a room temperature for 1 hour. The reaction mixture was added with methanol and water and extracted with chloroform 3 times. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1 to 10/1) to obtain 2-bromo-1-(benzyloxymethyl)-3,5-bis(methoxymethoxy)benzene (3.2 g, 70%).

후처리

  1. extractionextracted with chloroform 3 times
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1 to 10/1)

출처 및 근거

ORD 기록
ord-5334302b696f4a42ad884166bf4779dd
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07781485B2

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