Potassium Carbonate → HCID 66906613, compound

HRID 1690440Notes

Reaction equation

HRID 1690440 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+].[F: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]([F: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 680073-Fluorobenzyl bromideHCID 12223651Dimethyl 3-hydroxyphthalate

Product 1

HCID 66906613HCID 66906613, compoundYield 112.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred suspension of 3-hydroxyphthalic acid dimethyl ester (1.4 g, 6.7 mmol) in acetone (30 mL) and potassium carbonate (2.8 g, 20 mmol) was added 3-fluorobenzyl bromide (0.89 mL, 7.0 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-fluoro-benzyloxy)-phthalic acid dimethyl ester (2.4 g, 113% 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-ec4020cb38064e0db70f54d7accae98c
Source dataset
uspto-grants-2012_04
Patent number
US08153659B2

Reaction notes

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