2,3,4-Trimethoxybenzoic acid → 5-Bromo-2,3,4-trimethoxybenzoic acid

HRID 1042726

反応式

HRID 1042726 の反応式
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].CC([O-])=O.[Na+].[Br:21]Br>CC(O)=O.C(OCC)C>[Br:21][C:9]1[C:10]([O:14][CH3:15])=[C:11]([O:12][CH3:13])[C:3]([O:2][CH3:1])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6]

参加物

6

反応物 3

HCID 113082,3,4-Trimethoxybenzoic acidHCID 24408BromineHCID 517045Sodium Acetate

生成物 1

HCID 594278855-Bromo-2,3,4-trimethoxybenzoic acid

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 3283Diethyl Ether溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2,3,4-trimethoxybenzoic acid (4.7 g, 22 mmol) and NaOAc (5.5 g, 40 mmol) in 35 ml AcOH was added a solution of bromine (1.5 ml, 29 mmol) in 35 ml AcOH. The reaction became red in color, which quickly faded. The mixture was heated to 80° C. for 1 h, at which point it was cooled to ambient temperature. The material was partitioned between dichloromethane and water. The organic layer was removed and the aqueous layer was extracted once with dichloromethane. The combined organic layers were dried with Na2SO4, filtered, and concentrated to give an oil which solidified on standing. The material was dissolved in diethyl ether and hexanes. Concentration to ½ the volume resulted in precipitation of a white solid. Filtration provided the title compound as a white solid. MS m/z: 293 (M+H+); calc'd for C10H11BrO5: 291.1

後処理

  1. temperaturewas cooled to ambient temperature
  2. customThe material was partitioned between dichloromethane and water
  3. customThe organic layer was removed
  4. extractionthe aqueous layer was extracted once with dichloromethane
  5. dry with materialThe combined organic layers were dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oil which
  9. concentrationConcentration
  10. customresulted in precipitation of a white solid
  11. filtrationFiltration

出典と根拠

ORDレコード
ord-86887e954fa04ebb8c437c66b3067012
出典データセット
uspto-grants-2013_10
特許番号
US08557996B2

関連ノート

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