Acetonitrile → Bis(p-chlorophenyl)amine

HRID 589246Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.NO.[ClH:13].C([O-])([O-])=O.[K+].[K+].[CH3:20][C:21]#[N:22]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:22][C:21]2[CH:4]=[CH:3][C:2]([Cl:13])=[CH:7][CH:20]=2)=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 6342Acetonitrile

HCID 11430Potassium Carbonate

HCID 742994-Chlorophenylboronic acid

HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 234111Bis(p-chlorophenyl)amine

Conditions

Temperature: 70 °C

Procedure

Under air, a 500-mL rbf was charged with (4-chlorophenyl)boronic acid (15.0 g, 96.0 mmol, 1 eq.), NH2OH.HCl (8.0 g, 115 mmol, 1.2 eq.), CuBr (2.75 g, 19.18 mmol, 0.2 eq.), K2CO3 (19.89 g, 144.0 mmol, 1.5 eq.), and CH3CN (320 mL). The reaction mixture was stirred at 70° C. for 24 h. The completion of the reaction was monitored by TLC. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on a silica gel using 10%-20% EtOAc in hexanes to give the product as brown oil that solidifies when dried under vacuum.

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was purified by flash column chromatography on a silica gel using 10%-20% EtOAc in hexanes

Sources & evidence

ORD record: ord-c8ffc496ff8a4f36a63686dc5a044e11
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227986B2

Reaction notes

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