1,2,4,5-Tetrachlorobenzene → 1,2,3-Trichlorobenzene

HRID 975610

Reaction equation

HRID 975610 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1Cl.[BH4-].[Na+].[Cl-:13].[Li+]>[CH-]1[C-]=[C-][C-]=[C-]1.[CH-]1[C-]=[C-][C-]=[C-]1.Cl[Ti]Cl>[Cl:8][C:6]1[C:5]([Cl:9])=[C:4]([Cl:13])[CH:3]=[CH:2][CH:7]=1

Participants

5

Reactant 3

HCID 72701,2,4,5-TetrachlorobenzeneHCID 433294Lithium ChlorideHCID 4311764Sodium borohydride

Product 1

HCID 68951,2,3-Trichlorobenzene

Reagents, catalysts & solvents 1

HCID 416358Bis(cyclopentadienyl)titanium(IV) chlorideCatalyst

Conditions

Temperature
96 °C

Procedure

A flask equipped with a magnetic stir bar and a water cooled condenser with an oil bubbler was charged with 1,2,4,5-tetrachlorobenzene (648 mg, 3.0 mmol), sodium tetrahydridoborate (1135 mg, 30.0 mmol), bis(η5 -cyclopentadienyl)titanium dichloride (75 mg, 0.3 mmol) and 1-methyl-2pyrrolidine (NMP; 30.0 ml). The reaction mixture was heated at 96° C. in an oil bath. After 4.25 hours, lithium chloride (1.09 g, 30.0 mmol) was added. Aliquots were withdrawn by syringe, quenched with water, and extracted with diethyl ether. The ether layer was analyzed with the results shown in the following table. Only trichlorobenzene was produced.

Workup

  1. customA flask equipped with a magnetic stir bar and a water cooled condenser with an oil bubbler
  2. customAliquots were withdrawn by syringe
  3. customquenched with water
  4. extractionextracted with diethyl ether

Sources & evidence

ORD record
ord-afb72519c4d7429caf96dfaa4c7ee144
Source dataset
uspto-grants-1997_03
Patent number
US05608135

Linked notes

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