Potassium Carbonate → HCID 66906596, compound

HRID 1915148Notes

Reaction equation

HRID 1915148 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].C(=O)([O-])[O-].[K+].[K+].[Br:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br>CC(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([O:14][CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[C:23]([Br:22])[CH:24]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699793-Bromobenzyl bromideHCID 12223651Dimethyl 3-hydroxyphthalate

Product 1

HCID 66906596HCID 66906596, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred suspension of 3-hydroxyphthalic acid dimethyl ester (1.3 g, 6.2 mmol) in acetone (30 mL) and potassium carbonate (2.5 g, 18.4 mmol) was added 3-bromobenzyl bromide (1.6 g, 6.4 mmol) and refluxed overnight. The solvent was evaporated and the residue was partitioned between water (100 mL) and ethyl acetate (150 mL) and washed with water (2×100 mL). The combined organic phases was dried, concentrated and purified by flash column chromatography (EtOAc/Hexane) to give 3-(3-bromo-benzyloxy)-phthalic acid dimethyl ester (2.5 g, 109% crude yield). The product was used in the next step without further purification.

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between water (100 mL) and ethyl acetate (150 mL)
  4. washwashed with water (2×100 mL)
  5. customThe combined organic phases was dried
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (EtOAc/Hexane)

Sources & evidence

ORD record
ord-caa7b58f8377488c9cc6c8211d4a748f
Source dataset
uspto-grants-2013_12
Patent number
US08614328B2

Reaction notes

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