Reaction #2458

Reaction equation

Thiophosphoryl chloride

2,4-dimethylphenol

→

bis(2,4-dimethylphenyl) chlorothiophosphate

Yield 89.9%

Solvents

triethylamine

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe mixture was stirred for 2 hr
3. 3
   Temperatureand then heated
4. 4
   workup.STIRRINGstirred at 80° C. for a further 2 hr
5. 5
   Temperatureand then cooled
6. 6
   Filtrationfiltered
7. 7
   Otherto remove thriethylamine hydrochloride
8. 8
   workup.DISTILLATIONThe toluene was distilled under reduced pressure

Procedure

Thiophosphoryl chloride (17.0 g) was dissolved in tuoluene (250 cm3) and triethylamine (21.5 g) was added. The solution was stirred at 20° C. and 2,4-dimethylphenol (24.4 g) was added in portions during 1 hr. The mixture was stirred for 2 hr. and then heated and stirred at 80° C. for a further 2 hr. and then cooled and filtered to remove thriethylamine hydrochloride. The toluene was distilled under reduced pressure leaving bis(2,4-dimethylphenyl) chlorothiophosphate (oil, 30.6 g. 31P NMR in CDCl3, singlet 54.57 ppm downfield of H3 PO4).

Source