Cesium carbonate → Methyl 6-methoxybenzofuran-2-carboxylate

HRID 2113164

Reaction equation

HRID 2113164 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[OH:7][C:8]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:9]=1[CH:10]=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH3:6][O:5][C:3]([C:2]1[O:7][C:8]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:9]=2[CH:10]=1)=[O:4]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 3016964Methyl 6-methoxybenzofuran-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl bromoacetate (1.53 g, 10 mmol), 2-hydroxy-4-methoxybenzaldehyde (1.52 g, 10 mmol) and Cs2CO3 (6.5 g, 20 mmol) in DMF (100 mL) was stirred vigorously at 50° C. for 3 hrs and then at 150° C. for 5 min. The reaction was cooled, diluted with ethyl acetate and washed with water. The organic phase was dried and concentrated to give essentially pure 6-methoxy-benzofuran-2-carboxylic acid methyl ester as a solid.

Workup

  1. waitat 150° C. for 5 min
  2. temperatureThe reaction was cooled
  3. washwashed with water
  4. customThe organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bd952c834afe4e92806ea9bf045a73d9
Source dataset
uspto-grants-2009_04
Patent number
US07524882B2

Linked notes

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