Reaction #586131

Reaction equation

1-chloro-5-(2,6-dichloro-4-trifluoromethylphenyl)-2-nitrobenzene

sodium hydride

isopropyl mercaptan

hydrogen

→

[5-(2,6-dichloro-4-trifluoromethylphenyl)-2-nitrophenyl] isopropyl sulfide

Yield 90.3%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONwas added
3. 3
   Extractionextracted with 50 ml of ethyl acetate twice
4. 4
   WashThe ethyl acetate was washed with 100 ml of water twice
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe ethyl acetate was distilled off under reduced pressure
7. 7
   OtherPurification of the residue by silica gel column chromatography

Procedure

0.33 g (8.3 mmol) of 60% sodium hydride was stirred in 50 ml of N,N-dimethylformamide at room temperature while 0.7 g (9.2 mmol) of isopropyl mercaptan was added dropwise. After generation of hydrogen was over, 3.0 g (8.1 mmol) of 1-chloro-5-(2,6-dichloro-4-trifluoromethylphenyl)-2-nitrobenzene was added, and the reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into about 200 ml of ice-cold water and extracted with 50 ml of ethyl acetate twice. The ethyl acetate was washed with 100 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 3.0 g of [5-(2,6-dichloro-4-trifluoromethylphenyl)-2-nitrophenyl] isopropyl sulfide (yield 90.0%) as a yellow dough (nD20 1.5881).

Source