Ethanol → Ethyl 2-amino-3-bromo-5-methylbenzoate

HRID 43970

反応式

HRID 43970 の反応式
[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH2:17](O)[CH3:18]>>[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:3]=1[C:4]([O:6][CH2:17][CH3:18])=[O:5]

参加物

4

反応物 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 27744002-Amino-3-bromo-5-methylbenzoic acid

生成物 1

HCID 54594338Ethyl 2-amino-3-bromo-5-methylbenzoate収率 64%

実験手順

Ethanol (10 mL) was added to 2-amino-3-bromo-5-methylbenzoic acid (1.00 g, 4.4 mmol). While the mixture was stirred, thionyl chloride (1.03 g, 8.7 mmol) was added at room temperature, followed by stirring at 80° C. overnight. The reaction solution was concentrated, and then diluted with water under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=0/10, 4/6) to obtain 715 mg of the title compound as a pale yellow solid (64%).

後処理

  1. stirringby stirring at 80° C. overnight
  2. concentrationThe reaction solution was concentrated
  3. additiondiluted with water under ice-
  4. temperaturecooling
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with aqueous sodium bicarbonate solution and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=0/10, 4/6)

出典と根拠

ORDレコード
ord-afb07232ce8c4d14a2a461e01a8421a7
出典データセット
uspto-grants-2013_09
特許番号
US08536197B2

関連ノート

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