Chlorobenzene → HCID 12383333, compound

HRID 1641620Notes

Reaction equation

HRID 1641620 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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:17]1([C:13]2[CH:14]=[CH:15][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][C:9]=2[C:10]([OH:12])=[O:11])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 7964ChlorobenzeneHCID 10796Cesium carbonateHCID 12854(1,1'-Biphenyl)-3-carboxylic acidHCID 11371790Bis(adamantan-1-yl)(butyl)phosphane

Product 1

HCID 12383333HCID 12383333, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Palladium acetate (5.6 mg, 0.025 mmol), 3-phenylbenzoic acid (99 mg, 0.5 mmol) and 4-chlorobenzene (169 mg, 1.5 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 97 mg (71%) of a white solid was obtained. Analytical data are consistent with that of previously reported data.6 1H NMR (300 MHz, CDCl3) δ 7.36-7.50 (m, 10H), 7.63-7.66 (m, 2H), 7.75-7.78 (m, 1H), 8.15-8.18 (m, 1H). Carboxylate proton signal was not observed. The 1H NMR spectrum is shown in FIG. 43.

Sources & evidence

ORD record
ord-5256ace556fb487fb3e0590e802af3b6
Source dataset
uspto-grants-2012_02
Patent number
US08114993B2

Reaction notes

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