Sodium Bicarbonate → Methyl 5-bromobenzo[d][1,3]dioxole-4-carboxylate

HRID 617415Notes

Reaction equation

HRID 617415 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[C:11]([OH:13])=[O:12].[C:14]([O-])(O)=O.[Na+]>CO.S(=O)(=O)(O)O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 125141065-Bromobenzo(1,3)dioxole-4-carboxylic acid

Product 1

HCID 54551814Methyl 5-bromobenzo[d][1,3]dioxole-4-carboxylateYield 55%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

5-Bromo-1,3-benzodioxole-4-carboxylic acid (0.34 g, 1.39 mmol) was dissolved in methanol (25 mL). A few drops of concentrated sulfuric acid were added and the solution was heated to reflux for 60 h at which time TLC analysis indicated the reaction complete. The reaction was cooled and poured into a solution of 5% NaHCO3 (25 mL) and extracted with ethyl acetate. The organic layers were dried with magnesium sulfate and concentrated by rotary evaporation to afford 0.20 g of product (0.77 mmol, 55% yield) as an off-white solid. 1H NMR (CDCl3) δ 7.11 (d, J=8.3 Hz, 1H), 6.78 (d, J=8.3 Hz, 1H), 6.09 (s, 2H), 3.95 (s, 3H).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 60 h at which time TLC analysis
  3. temperatureThe reaction was cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layers were dried with magnesium sulfate
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-6e1e2af0b2d54b12a8d42a5f9f659b1c
Source dataset
uspto-grants-1999_09
Patent number
US05948817

Reaction notes

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