2-Bromopropane → 3-Methyl-4-isopropoxy-benzofuran-2-carboxylic acid tert-butyl ester

HRID 29352Notes

Reaction equation

HRID 29352 reaction equation
[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH:20]([CH3:22])[CH3:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH:20]([CH3:22])[CH3:21])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 138494564-Hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

Product 1

HCID 687150563-Methyl-4-isopropoxy-benzofuran-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester (200 mg, 0.8 mmol) in 4 mL of DMF was added 2-bromopropane (0.5 mL), and K2CO3 (200 mg). The mixture was stirred at room temperature overnight. The mixture was washed with brine and extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine. Removal of the solvent gave 176 mg of 3-methyl-4-isopropoxy-benzofuran-2-carboxylic acid tert-butyl ester as colorless crystals.

Workup

  1. washThe mixture was washed with brine
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate layers were washed with brine
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-6b66946759b04db79b8dd1fc18c6e611
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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