2-Bromopropane → HCID 68716041, compound

HRID 29338Notes

Reaction equation

HRID 29338 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:8]=2[CH:9]=1)=[O:4].Br[CH:16]([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:16]([O:14][C:10]1[C:8]2[CH:9]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[O:6][C:7]=2[CH:13]=[CH:12][CH:11]=1)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 14494065Methyl 4-hydroxybenzofuran-2-carboxylate

Product 1

HCID 68716041HCID 68716041, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.41 g (2.13 mmol) of 4-hydroxy-2-benzofurancarboxylic acid methyl ester in 7 mL of DMF was added 0.80 mL (8.54 mmol) of 2-bromopropane and 1.18 g (8.54 mmol) of potassium carbonate. The reaction was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, and the residue was extracted with ethyl acetate. The organic layer washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 0.49 g of methyl 4-isopropoxy-1-benzofuran-2-carboxylate. Yield ˜100%; m.p. 43-45° C.; MS: 235.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic layer washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15c5f1d5dfe849a5a6c5355f7b711ebf
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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