Ammonium → HCID 67354738, compound

HRID 1424778Notes

Reaction equation

HRID 1424778 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:11]=3[C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1.[CH:23](Br)([CH3:25])[CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+].[NH4+]>CN1C(=O)CCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:18][C:11]=3[C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 223AmmoniumHCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 46172351Ethyl 2-(4-chlorophenyl)-5-hydroxy-1-benzofuran-3-carboxylate

Product 1

HCID 67354738HCID 67354738, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 2-(4-chlorophenyl)-5-hydroxybenzofuran-3-carboxylate (26 g, 0.051 mol) in NMP (160 mL) was added isopropyl bromide (15 mL), then cesium carbonate (33 g, 0.101 mol) was added. The reaction mixture was stirred in a 60° C. oil bath for 20 hrs then cooled to ambient temperature. The reaction mixture was treated with 5% ammonium solution and stirred for 15 min. This mixture was then diluted with water and extracted with hexane. The organic layer was washed with water, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give ethyl 2-(4-chlorophenyl)-5-isopropoxybenzofuran-3-carboxylate (15 g, 82%).

Workup

  1. temperaturethen cooled to ambient temperature
  2. stirringstirred for 15 min
  3. extractionextracted with hexane
  4. washThe organic layer was washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7325a15498a4dd5974da9c6b6edbdd8
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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