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

HRID 1670719
ノート
印刷プレビュー

反応式

HRID 1670719 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 67553
Tetrabutylammonium Iodide
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5ad6e7ba929e47ae901675011fb6676b
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07994189B2

反応ノート

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