O-Xylene → Benzenamine, 2-chloro-5-(trifluoromethyl)-

HRID 1600409Notes

Reaction equation

HRID 1600409 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-])=O.C1(C)C(C)=CC=CC=1.P.[OH-].[Na+]>Cl[Pd]Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][C:3]=1[NH2:12]

Participants

7

Reactant 4

HCID 7237O-XyleneHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 14798Sodium HydroxideHCID 24404Phosphine

Product 1

HCID 8475Benzenamine, 2-chloro-5-(trifluoromethyl)-

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Procedure

A degassed solution of 40 mmol of 2-chloro-5-trifluoromethylnitrobenzene (starting material) and 40 ml of xylene are placed in an autoclave (volume: 200 ml). 3.0 mmol of BINAS (in the form of 17.3 g of an aqueous solution containing 0.173 mol of BINAS/kg of solution) as phosphine and 2.4 g (60 mmol) of NaOH, 23.8 ml of H2O and 1.0 mmol of PdCl2 are added. The pH is from 10.5 to 11.0.

Workup

  1. additionare added

Sources & evidence

ORD record
ord-937ff879706c4f09aac04f8fa2a26268
Source dataset
uspto-grants-1998_04
Patent number
US05744643

Reaction notes

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