4-Nitrobenzoyl chloride → 4-Chloro-4'-nitrobenzophenone

HRID 926468Notes

Reaction equation

HRID 926468 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[N+:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)([O-:13])=[O:12].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]([C:17]2[CH:16]=[CH:15][C:14]([N+:11]([O-:13])=[O:12])=[CH:22][CH:21]=2)=[O:19])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 62657Potassium Phosphate, TribasicHCID 742994-Chlorophenylboronic acid

Product 1

HCID 3477714-Chloro-4'-nitrobenzophenone

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of (4-chlorophenyl)boronic acid (1.50 g, 9.59 mmol), 4-nitrobenzoyl chloride (1.78 g 9.59 mmol), bis(triphenylphosphine)palladium(II) chloride (0.137 g, 0.192 mmol) and K3PO4 (3.34 g, 19.2 mmol) in toluene (30 mL) was treated as described in WO 2010/015355 to provide the title compound.

Workup

  1. additionwas treated

Sources & evidence

ORD record
ord-26fc8aeaa09d48a88b9413b56d909cef
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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