Cesium carbonate → Methyl 3-(3-(((4-bromo-3-methylphenyl)methyl)oxy)phenyl)propanoate

HRID 1662310Notes

Reaction equation

HRID 1662310 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]Cl)=[CH:23][C:22]=1[CH3:29]>CN(C=O)C.O>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][O:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=2)=[CH:23][C:22]=1[CH3:29]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1512675Methyl 3-(3-hydroxyphenyl)propionateHCID 189606101-Bromo-4-(chloromethyl)-2-methylbenzene

Product 1

HCID 57705740Methyl 3-(3-(((4-bromo-3-methylphenyl)methyl)oxy)phenyl)propanoateYield 90.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To flask containing methyl 3-(3-hydroxyphenyl)propanoate (available from Aagile Labs Division of Tyger Scientific) (0.25 g, 1.387 mmol) and cesium carbonate (0.5876 g, 1.804 mmol) in DMF (8 mL), was added 1.2 (0.3654 g, 1.665 mmol). The resulting mixture was then stirred overnight. The reaction was diluted with water and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and then purified by combiflash (0 to 20% EtOAc/hexane) to provide 1.3 (0.4575 g, 90.78% yield). MS ESI (pos.) m/e: 382.0 (M+H2O)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by combiflash (0 to 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-ddb01c2074b141bda272d99f1161faa4
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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