Tetrahydrofuran → HCID 178506744, compound

HRID 2082786Notes

Reaction equation

HRID 2082786 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.N#N.C1(C)C=CC=CC=1.C([Li:35])CCC>CCCCCC>[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([Li:35])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 89970Benzene, 1-bromo-4-(phenylsulfonyl)- (9CI)HCID 69791645HCID 69791645, compoundHCID 178418339Butyllithium

Product 1

HCID 178506744HCID 178506744, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 30 grams (0.1 mole) of 4-bromophenyl phenyl sulfone in 500 ml. of tetrahydrofuran was cooled to -100° C. in a liquid nitrogen-toluene slush, and 42 ml. (0.1 mole) of 2.38 M n-butyl lithium in hexane was added, forming 4-phenylsulfonyl-phenyl lithium. After about 10 minutes, 9.5 grams (0.05 mole) of diethyl dichlorophosphoramide was added, and the reaction mixture was allowed to warm slowly to room temperature, and then to stand a room temperature for 18 hours, forming diethyl bis [4-(phenylsulfonyl)phenyl] phosphoramide. Next, 125 ml. of 6 M HCl was added, and the reaction mixture was heated under reflux for 4 hours to hydrolyze the phosphoramide group. The tetrahydrofuran was removed by distillation, and 7.5 grams of almost white solid, M.P. 115°-130° C., was collected by filtration. This solid was recrystallized from tetrahydrofuran to give 7 grams (28% yield) of the bis[4-(phenylsulfonyl)phenyl] phosphinic acid product, m.p. 155°-165° C.

Sources & evidence

ORD record
ord-e50ae00ac6544a8c9ed36b7e630f4460
Source dataset
uspto-grants-1978_04
Patent number
US04082793

Reaction notes

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