Potassium Carbonate → Methyl 4-(2-bromo-4,5-dimethoxybenzyloxy)-2-hydroxybenzoate

HRID 2167117Notes

Reaction equation

HRID 2167117 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].[Br:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[CH:24][C:21]=1[CH2:22]Br>CC(C)=O>[Br:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[CH:24][C:21]=1[CH2:22][O:18][C:16]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([OH:7])[CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16523Methyl 2,4-DihydroxybenzoateHCID 110342482-Bromo-4,5-dimethoxybenzyl bromide

Product 1

HCID 89464825Methyl 4-(2-bromo-4,5-dimethoxybenzyloxy)-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (1.12 g) was added to a solution of methyl 2,4-dihydroxybenzoate (454 mg) and 2-bromo-4,5-dimethoxybenzyl bromide (1.0 g) in dry acetone (80 ml). The reaction mixture was heated to reflux at 80° C. for 4 hours. The solvents were removed under vacuum and the residue was re-dissolved in DCM and washed with water (3×). The organic layer was passed through a hydrophobic frit and concentrated under vacuum. The crude residue was purified by chromatography on silica gel, eluting with petrol and increasing amounts of ethyl acetate.

Workup

  1. temperatureThe reaction mixture was heated
  2. customThe solvents were removed under vacuum
  3. dissolutionthe residue was re-dissolved in DCM
  4. washwashed with water (3×)
  5. concentrationconcentrated under vacuum
  6. customThe crude residue was purified by chromatography on silica gel
  7. washeluting with petrol
  8. temperatureincreasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-8286cb9344cd46ddaac2e2ce705c6322
Source dataset
uspto-grants-2015_06
Patent number
US09044463B2

Reaction notes

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