2-Bromopropane → Ethyl 5-bromo-3-methyl-4-[(propan-2-yl)oxy]-1-benzofuran-2-carboxylate

HRID 29473Notes

Reaction equation

HRID 29473 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([Br:16])=[C:12]([OH:17])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH:25]([CH3:27])[CH3:26]>CN(C=O)C>[Br:16][C:13]1[CH:14]=[CH:15][C:8]2[O:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:10]([CH3:11])[C:9]=2[C:12]=1[O:17][CH:25]([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 125429705-Bromo-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 53428887Ethyl 5-bromo-3-methyl-4-[(propan-2-yl)oxy]-1-benzofuran-2-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 0.50 g (1.7 mmole) of ethyl 5-bromo-4-hydroxy-3-methyl-1-benzofuran-2-carboxylate (Example 119, Step 1) in 7 mL DMF was added 0.51 g (3.75 mmole) of potassium carbonate and 0.48 mL (3 mmole) of 2-bromopropane and the reaction was stirred at room temperature overnight. The solvent was concentrated in vacuo, and the residue was extracted with ethyl acetate and water. The organic layer washed with water and brine, dried over sodium sulfate, filtered, and concentrated to provide 0.58 g of ethyl 5-bromo-4-isopropoxy-3-methyl-1-benzofuran-2-carboxylate. Yield: 100%; m.p. 48-50° C.; MS: 341.0 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-62a3dcf3a45e48b883368175bcb8307f
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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