Cesium carbonate → HCID 66597032, compound

HRID 1518622Notes

Reaction equation

HRID 1518622 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[C:18]1(OB(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[N+:15]([C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:2]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 78412Phenyl dihydrogen orthoborateHCID 19989839HCID 19989839, compound

Product 1

HCID 66597032HCID 66597032, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

3-(4-Bromo-3-nitrobenzoyl)propionic acid (45.3 g, 150.0 mmol) was dissolved in 1,4-dioxane (400 mL), thereto were added phenyl boric acid (27.4 g, 225.0 mmol), cesium carbonate (146.6 g, 450.0 mmol), 1,1-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (3.7 g, 4.5 mmol), and purified water (150 mL), and the reaction mixture was stirred under a nitrogen flow at 80° C. for 18 hours. The reaction solution was filtered through celite, alumina, and Florisil, and, thereafter, the aqueous layer was separated. The organic layer was extracted with a dilute aqueous solution of sodium hydroxide. After the aqueous layers were combined and washed with ethyl acetate, the layer was acidified, under ice-water cooling, with 6 M hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 3-(3-nitro-4-phenylbenzoyl)propionic acid (39.4 g).

Workup

  1. custompurified water (150 mL)
  2. filtrationThe reaction solution was filtered through celite, alumina, and Florisil
  3. customthe aqueous layer was separated
  4. extractionThe organic layer was extracted with a dilute aqueous solution of sodium hydroxide
  5. washwashed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dfa62ed57fa34fd9b30e10387706c8fb
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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