Methyl 4-bromobenzoate → Methyl Benzoate

HRID 2216282Notes

Reaction equation

HRID 2216282 reaction equation
O1CCOCC1.[CH3:7][O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1.COCCN1CCNCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C>[CH3:7][O:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 12081Methyl 4-bromobenzoateHCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 27346381-(2-Methoxyethyl)piperazine

Product 1

HCID 7150Methyl Benzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To 10 ml of 1,4-dioxan is added 0.645 g (3.0 mmol) of methyl-4-bromobenzoate 0.519 g (3.6 mmol) of 1-(2-methoxy-ethyl-piperazine, 0.892 g (8.47 mmol) of potassium phosphate, 0.177 g (0.45 mmol) of 2-dicycohexylphosphino-2′-(N,N-dimethylamino)biphenyl and 0.137 g (0.15 mmol) tris-(benzylideneacetone)palladium (0). The resulting reaction mixture is stirred under argon for 5 hours at 100° C., then cooled to room temperature, diluted with ethyl acetate and filtered. The filtrate is washed once with H2O and once with brine, the organic layer separated and dried over Na2SO4. Purification of the crude product by flash chromatography (dichloromethane/methanol) yields 0.52 g of 4-[4-(2-methoxy-ethyl)-piperazin-1-yl)]benzoic acid methyl ester as a solid.

Workup

  1. customThe resulting reaction mixture
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. washThe filtrate is washed once with H2O and once with brine
  5. customthe organic layer separated
  6. dry with materialdried over Na2SO4
  7. customPurification of the crude product by flash chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-eb71949554154dd0ac8446d9f681a659
Source dataset
uspto-grants-2006_09
Patent number
US07112589B2

Reaction notes

Loading…