Chlorobenzene → HCID 45790716, compound

HRID 1641617Notes

Reaction equation

HRID 1641617 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].Cl[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2)CCC.C([O-])([O-])=O.[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[C:14]1([C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=[CH:10][C:6]=2[C:7]([OH:9])=[O:8])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 7964ChlorobenzeneHCID 84973-Nitrobenzoic acidHCID 10796Cesium carbonateHCID 11371790Bis(adamantan-1-yl)(butyl)phosphane

Product 1

HCID 45790716HCID 45790716, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Palladium acetate (5.6 mg, 0.025 mmol), 3-nitrobenzoic acid (84 mg, 0.5 mmol) and 4-chlorobenzene (283 mg, 2.5 mmol), butyldi-1-adamantylphosphine (19.2 mg, 0.05 mmol, Cs2CO3 (358 mg, 1.1 mmol), molecular sieves 3 Å (155 mg) and anhydrous DMF (2.5 mL). After flash chromatography and preparative HPLC 79 mg (65%) of a white solid was obtained. Analytical data are consistent with that of previously reported data.3 1H NMR (300 MHz, CDCl3) δ 7.32-7.37 (m, 2H), 7.42-7.46 (m, 3H), 7.57 (d, J-8.4 Hz, 1H), 8.40 (dd, J-8.4 Hz, 2.1 Hz, 1H), 8.80 (d, J-2.1 Hz, 1H). Carboxylate proton signal was not observed. The 1H NMR spectrum is shown in FIG. 37.

Sources & evidence

ORD record
ord-42d5478450174dab9c46cf8861dd907e
Source dataset
uspto-grants-2012_02
Patent number
US08114993B2

Reaction notes

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