2-Isopropylphenol → Bis(2-isopropylphenyl) chlorothiophosphate

Reaction equation

[H-].[Na+].[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])([CH3:5])[CH3:4].[P:13]([Cl:17])(Cl)(Cl)=[S:14]>C1(C)C=CC=CC=1>[P:13]([Cl:17])([O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:3]([CH3:5])[CH3:4])([O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:3]([CH3:5])[CH3:4])=[S:14]

Participants

Procedure

Sodium hydride (38.0 g of 80% suspension in mineral oil) was added to a stirred solution of 2-isopropylphenol (139.2 g) and thiophosphoryl chloride (84.5 g) in toluene (500 cm3) at such a rate that the reaction temperature did not rise above 65° C. After stirring for a further 0.5 hr at ambient temperature, the solution was extracted twice with water (250 cm3 portions), separated, dried (MgSO4) and concentrated by distillation of solvents under reduced pressure yielding crude bis(2-isopropylphenyl) chlorothiophosphate, a brown oil (164.2 g); 31P NMR in CDCl3, singlet 53.0 ppm downfield of H3PO4). Of this material, 54.0 g were reacted with ammonia by the procedure of Example 9 yielding crude bis(2-isopropylphenyl)thiophosphoramide) (50.0 g; 31PNmr, singlet δ=58.8 ppm).