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

HRID 576384Notes

Reaction equation

HRID 576384 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-657ab8abe50249db9a1f2ecc8266728a
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

Loading…