Cesium carbonate → HCID 68435211, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[OH:11].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:52]([C:56]#[CH:57])([CH3:55])([CH3:54])[CH3:53]>[Pd](Cl)Cl.C(#N)C.C(#N)C.C(#N)C>[C:52]([C:56]1[O:11][C:3]2[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=2[CH:57]=1)([CH3:55])([CH3:54])[CH3:53]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
2-Bromo-6-nitrophenol (500 mg, 2.29 mmol), bis(acetonitrile) palladium (II) chloride (12 mg, 0.05 mmol), 2-dicylohexylphosphino-2′,4′,6′-triisopropylbiphenyl (68 mg, 0.14 mmol), cesium carbonate (1.95 g, 6 mmol) and tert-butylacetylene (577 mg, 7 mmol) were dissolved 5 mL acetonitrile in a sealed tube and heated at 75° C. overnight. The reaction mixture was directly chromatographed (silica gel, heptane/ethyl acetate 9:1/4:1/1:1) to yield 2-tert-butyl-7-nitro-benzofuran as an off-white solid (185 mg, 37%).
Workup
- customThe reaction mixture was directly chromatographed (silica gel, heptane/ethyl acetate 9:1/4:1/1:1)
Sources & evidence
- ORD record
- ord-90ae757bf85c464596377ff5abdaadc8
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07825253B2
Reaction notes
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