Potassium Carbonate → Methyl 5-bromo-3-methylbenzofuran-2-carboxylate

HRID 2091390Notes

Reaction equation

HRID 2091390 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:8]([CH3:9])[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 42967109Methyl 5-bromo-3-methylbenzofuran-2-carboxylateYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (200 mL) of 1-(5-bromo-2-hydroxyphenyl)ethanone (25.0 g) in N,N-dimethylformamide were added potassium carbonate (24.0 g) and methyl bromoacetate (11.5 mL) at room temperature, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was filtered, 1,8-diazabicyclo[5.4.0]undec-7-ene (23.2 mL) was added to the filtrate, and the mixture was stirred at 100° C. for 3 hr. The reaction mixture was allowed to cool to room temperature, and ice water was added. The precipitate was washed with ethanol-water to give the title object compound (16.8 g, 52%) as a pale-red solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. addition1,8-diazabicyclo[5.4.0]undec-7-ene (23.2 mL) was added to the filtrate
  3. stirringthe mixture was stirred at 100° C. for 3 hr
  4. temperatureto cool to room temperature
  5. additionice water was added
  6. washThe precipitate was washed with ethanol-water

Sources & evidence

ORD record
ord-77ebe215a9c14134a128ad2acfd525cf
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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