4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → Benzenamine, 2-chloro-5-(trifluoromethyl)-

HRID 1600408Notes

Reaction equation

HRID 1600408 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.C1C=C(S([O-])(=O)=O)C=C(P(C2C=CC=C(S([O-])(=O)=O)C=2)C2C=CC=C(S([O-])(=O)=O)C=2)C=1.[Na+].[Na+].[Na+].P.[OH-].[Na+]>Cl[Pd]Cl.O.C1(C)C(C)=CC=CC=1>[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

8

Reactant 4

HCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 14798Sodium HydroxideHCID 24404PhosphineHCID 6099338Trisodium 3,3',3''-phosphinetriyltris(benzene-1-sulphonate)2×

Product 1

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

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 7237O-XyleneSolvent

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). 5.0 mmol of TPPTS (in the form of 9.2 g of an aqueous solution containing 0.546 mol of TPPTS/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-963937db44234e6586d262d7305c6826
Source dataset
uspto-grants-1998_04
Patent number
US05744643

Reaction notes

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