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Citric Acid → 3-(2-Bromo-6-ethoxy-4-formylphenoxymethyl)-benzoic acid methyl ester

HRID 1670719
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HRID 1670719 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]Br)[CH:5]=1.C([O-])([O-])=O.[K+].[K+].[Br:19][C:20]1[C:21]([OH:31])=[C:22]([O:28][CH2:29][CH3:30])[CH:23]=[C:24]([CH:27]=1)[CH:25]=[O:26].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:31][C:21]2[C:22]([O:28][CH2:29][CH3:30])=[CH:23][C:24]([CH:25]=[O:26])=[CH:27][C:20]=2[Br:19])[CH:5]=1
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참가 물질

8

반응물 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehyde

생성물 1

HCID 866244083-(2-Bromo-6-ethoxy-4-formylphenoxymethyl)-benzoic acid methyl ester

시약·촉매·용매 3

HCID 67553
Tetrabutylammonium Iodide
촉매
HCID 962Water용매
HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

3-Bromomethylbenzoic acid methyl ester (0.77 g), K2CO3 (1.0 g) and a catalytic amount of n-Bu4NI were added to a solution of 5-bromo-3-ethoxy-4-hydroxybenzaldehyde (0.75 g) in 10 mL DMF and the reaction mixture was stirred at 70° C. for 1 h. A solution of 3% citric acid in water was added and the reaction mixture was extracted with ethyl acetate. The organic phases were washed with water and brine, dried over MgSO4 and concentrated. The title compound was obtained after flash column chromatography (silica gel, heptane/ethyl acetate (1/4, v/v), Rf=0.25).

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic phases were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5ad6e7ba929e47ae901675011fb6676b
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07994189B2

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