Dichloromethane → HCID 59385322, compound

HRID 2356793Notes

Reaction equation

HRID 2356793 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)([O-:16])=[O:15].C([O-])([O-])=O.[Na+].[Na+].ClCCl>C1(C)C=CC=CC=1.CCOC(C)=O.O.O1CCOCC1>[CH3:13][O:12][C:4]1[CH:3]=[C:2]([C:20]2[CH:21]=[CH:22][C:17]([N+:14]([O-:16])=[O:15])=[CH:18][CH:19]=2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27735524-Nitrophenylboronic acidHCID 15128242Methyl 4-bromo-2-methoxybenzoate

Product 1

HCID 59385322HCID 59385322, compoundYield 61%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 4-bromo-2-methoxybenzoate (0.95 g, 3.9 mmol) and 4-nitrophenylboronic acid (1.29 g, 7.75 mmol) in toluene (10 mL) was added Na2CO3 (1.85 g, 17.4 mmol), 1,1-bis(diphenylphosphino)ferrocenepalladium(II) chloride complex with dichloromethane (0.06 g, 0.08 mmol), 1,4-dioxane (5 mL), and water (5 mL). The mixture was heated at reflux for 3 h and then allowed to cool to rt. The mixture was diluted with EtOAc and water, and the organic layer was isolated, dried over MgSO4, and concentrated in vacuo. The material was purified by column chromatography (25% EtOAc in hexanes), yielding 0.675 g (61%) of the title compound. LC/MS m/z 287.9 (MH+); retention time 3.14 min.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. customthe organic layer was isolated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe material was purified by column chromatography (25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-325c9f9ddff74e09b345626938088f32
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

Loading…