Sodium Carbonate → 2-Amino-6-chloro-5-(3,5-dichlorophenyl)benzonitrile

HRID 363760Notes

Reaction equation

HRID 363760 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7](Br)=[C:6]([Cl:11])[C:3]=1[C:4]#[N:5].[Cl:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[C:17]([Cl:19])[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([C:15]2[CH:14]=[C:13]([Cl:12])[CH:18]=[C:17]([Cl:19])[CH:16]=2)=[C:6]([Cl:11])[C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343313,5-Dichlorophenylboronic acidHCID 543850846-Amino-3-bromo-2-chlorobenzonitrile

Product 1

HCID 541017212-Amino-6-chloro-5-(3,5-dichlorophenyl)benzonitrileYield 63.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

This compound was prepared in a manner analogous to that of Step D of Example 1, using 2.3 grams (0.010 mole) of 2-amino-5-bromo-6-chlorobenzonitrile (prepared as in Step A of Example 2), 2.9 grams (0.015 mole) of 3,5-dichlorophenylboronic acid, 0.1 gram (catalyst) of tetrakis(triphenylphosphine)palladium(0), and 30 mL of aqueous 2M sodium carbonate in 75 mL of toluene. The solid product was recrystallized from toluene, yielding 1.9 grams of 2-amino-6-chloro-5-(3,5-dichlorophenyl)benzonitrile. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step D of Example 1
  2. customThe solid product was recrystallized from toluene

Sources & evidence

ORD record
ord-f25f667245b740d1ba62ac44e3df1016
Source dataset
uspto-grants-1999_02
Patent number
US05874579

Reaction notes

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