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Water → Methyl 5-bromo-3-chloro-4-methoxy-2-(methoxymethoxy)benzoate

HRID 629383
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HRID 629383 반응식
[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([Cl:13])[C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[CH3:18][O:19][CH2:20]Cl.O>C1COCC1>[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([Cl:13])[C:5]([O:12][CH2:18][O:19][CH3:20])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]
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6

반응물 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 118468147Methyl 5-bromo-3-chloro-2-hydroxy-4-methoxybenzoate

생성물 1

HCID 118468157Methyl 5-bromo-3-chloro-4-methoxy-2-(methoxymethoxy)benzoate수율 53.6%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of methyl 5-bromo-3-chloro-2-hydroxy-4-methoxybenzoate (5.00 g) in THF (120 mL) was added sodium hydride (1.01 g) under ice-cooling, and the mixture was stirred for 1 hr under nitrogen atmosphere. To this reaction mixture was added dropwise chloromethyl methyl ether (1.63 g), and the mixture was stirred at 20° C. for 16 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (3.08 g).

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at 20° C. for 16 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether)

출처 및 근거

ORD 기록
ord-5bc0d4ac9bf04783b8db2187b9c9219c
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09315458B2

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