Calcium Carbonate → Methyl 3,5-dibromo-4-(hydroxymethyl)benzoate

HRID 394213Notes

Reaction equation

HRID 394213 reaction equation
Br[CH2:2][C:3]1[C:12]([Br:13])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[Br:14].C([O-])([O-])=[O:16].[Ca+2]>O1CCOCC1.O>[Br:14][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([Br:13])[C:3]=1[CH2:2][OH:16])[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 10112Calcium CarbonateHCID 22647948Methyl 3,5-dibromo-4-(bromomethyl)benzoate2×

Product 1

HCID 22648140Methyl 3,5-dibromo-4-(hydroxymethyl)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of methyl 3,5-dibromo-4-(bromomethyl)benzoate (INTERMEDIATE 24) (12.53 g, 32.4 mmol, 1 eq) in dioxane (100 mL) and water (100 mL) was added CaCO3 (8.1 g, 81 mmol, 2.5 eq). The mixture was warned to and stirred at 100° C. until reaction was complete by HPLC analysis. The mixture was cooled and the solvent removed under reduced pressure. The residue was diluted with water and extracted 3× with CH2Cl2. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated giving methyl 3,5-dibromo-4-(hydroxymethyl)benzoate. The material was taken immediately to the next step.

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent removed under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted 3× with CH2Cl2
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f98205ee875a4107b9a4a08c7534c4ca
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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