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Water → Methyl 4-[(acetyloxy)methyl]-3-bromobenzoate

HRID 501802
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HRID 501802 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12]Br)[C:5]([O:7][CH3:8])=[O:6].[C:14]([O-:17])(=[O:16])[CH3:15].[K+].O.C(OCC)(=O)C>CN(C)C=O>[C:14]([O:17][CH2:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[Br:1])(=[O:16])[CH3:15]
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참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 517044Potassium AcetateHCID 10804694Methyl 3-bromo-4-(bromomethyl)benzoate

생성물 1

HCID 57543439Methyl 4-[(acetyloxy)methyl]-3-bromobenzoate수율 63.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

10.85 g of methyl 3-bromo-4-(bromomethyl)benzoate was dissolved in 108 mL of N,N-dimethylformamide, to which 3.46 g of potassium acetate was added at room temperature, and this solution was stirred for 17.5 hours at the same temperature. The reaction mixture was added to a mixture of water and ethyl acetate, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=10:1] to yield 6.43 g of methyl 4-[(acetyloxy)methyl]-3-bromobenzoate as white solid.

후처리

  1. additionwas added at room temperature
  2. customthe organic phase was separated
  3. washAfter the resultant organic phase was washed with water
  4. dry with materiala saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=10:1]

출처 및 근거

ORD 기록
ord-a46ea5b9693d4b6d9bc0919224967d5e
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07772285B2

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