2-Methyl-2-butene → 5-Bromo-2-chloro-3,4-dimethoxybenzoic acid

HRID 2206756ノート

反応式

HRID 2206756 の反応式
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([O:11][CH3:12])[C:5]([Cl:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].CC(=CC)C.[OH:20]P([O-])(O)=O.[K+].[O-]Cl=O.[Na+]>CC(O)(C)C>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([O:11][CH3:12])[C:5]([Cl:10])=[C:6]([CH:9]=1)[C:7]([OH:20])=[O:8]

参加物

6

反応物 4

HCID 105532-Methyl-2-buteneHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 867140735-Bromo-2-chloro-3,4-dimethoxybenzaldehyde

生成物 1

HCID 867140755-Bromo-2-chloro-3,4-dimethoxybenzoic acid収率 99.6%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

To the mixture of aldehyde 157 (11.1 g, 39.4 mmol), 2-methyl-2-butene (105 mL, 985 mmol) in t-BuOH (300 mL) was added KH2PO4 (38 g, 276 mmol). NaClO2 (32 g, 355 mmol, dissolved in H2O (160 mL)) was added to the reaction mixture. The mixture was stirred at r.t. for 15 hours. The mixture was evaporated in vacuo to remove the solvent. The residue was extracted with EtOAc/aq. 5% HCl solution (500 mL/300 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound 158 (11.6 g, 99%).

後処理

  1. customThe mixture was evaporated in vacuo
  2. customto remove the solvent
  3. extractionThe residue was extracted with EtOAc/aq
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d0bb5f3dc0184b568a4c30d0e195550e
出典データセット
uspto-grants-2016_06
特許番号
US09371303B2

反応ノート

読み込み中…