Cesium carbonate → 1-(5-Tert-butyl-2-methoxy-3-nitro-phenyl)-azetidin-2-one

HRID 735806Notes

Reaction equation

HRID 735806 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[O:15][CH3:16].[NH:17]1[CH2:20][CH2:19][C:18]1=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+]>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[C:8]([C:6]1[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[C:3]([O:15][CH3:16])=[C:2]([N:17]2[CH2:20][CH2:19][C:18]2=[O:21])[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1367212-AzetidinoneHCID 575500241-Bromo-5-(tert-butyl)-2-methoxy-3-nitrobenzene

Product 1

HCID 575500231-(5-Tert-butyl-2-methoxy-3-nitro-phenyl)-azetidin-2-oneYield 106.6%

Reagents, catalysts & solvents 2

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalyst

Conditions

Temperature
100 °C

Procedure

An oven-dried Schlenk tube was charged with the above nitroanisole (500 mg, 1.74 mmol), 2-azetidinone (150 mg, 2.1 mmol), tris(dibenzylideneacetone) dipalladium(0) (32 mg, 0.035 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (58 mg, 0.1 mmol) and cesium carbonate (795 mg, 2.44 mmol). The tube was capped with a rubber septum, purged with argon and 1,4-dioxane (7 mL) was then added through the septum via a syringe. The tube was sealed with a teflon screwcap and the reaction mixture was stirred at 100° C. for 20 h. The reaction mixture was cooled to room temperature, diluted with EtOAc (100 mL), washed with water, brine and dried over anhydrous Na2SO4. The solvent was removed in vacuo, and the crude product was purified by column:chromatography (2:1 hexane-EtOAc) to give 1-(5-tert-butyl-2-methoxy-3-nitro-phenyl)-azetidin-2-one (516 mg, quantitative).

Workup

  1. customThe tube was capped with a rubber septum
  2. custompurged with argon and 1,4-dioxane (7 mL)
  3. additionwas then added through the septum via a syringe
  4. customThe tube was sealed with a teflon screwcap
  5. temperatureThe reaction mixture was cooled to room temperature
  6. additiondiluted with EtOAc (100 mL)
  7. washwashed with water, brine
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe solvent was removed in vacuo
  10. customthe crude product was purified by column

Sources & evidence

ORD record
ord-ebf68852841341368fdd806d72320493
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

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