Hydrochloric Acid → bis(3-methylphenyl)phosphinic acid

HRID 1086008Notes

Reaction equation

HRID 1086008 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[Mg].C(N(CC)[P:13](Cl)([O-:15])=[O:14])C.Cl>>[C:4]1([CH3:8])[CH:5]=[CH:6][CH:7]=[C:2]([P:13]([C:2]2[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=2)(=[O:14])[OH:15])[CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 115603-BromotolueneHCID 5462224MagnesiumHCID 20059535HCID 20059535, compound

Product 1

HCID 262047bis(3-methylphenyl)phosphinic acid

Procedure

That is, m-bromotoluene (II) is reacted with metallic magnesium to prepare a Grignard reagent (III) which is then condensed with N,N-diethylamidochlorophosphate (IV) obtained by the process described in G. M. Kosolapoff et al., J. Am. Chem. Soc., Vol. 71, pp. 369-370 (1949), followed by hydrolysis with hydrochloric acid to obtain di-(m-tolyl)phosphinic acid (V). The compound (V) is reacted with thionyl chloride. After removing excess thionyl chloride, the reaction mixture is recrystallized from a mixed solution of benzene and hexane to obtain di-(m-tolyl)phosphonyl chloride (VI).

Workup

  1. customobtained by the process

Sources & evidence

ORD record
ord-27b4d8d2ff854867ae341c5de0db50f5
Source dataset
uspto-grants-1991_04
Patent number
US05012002

Reaction notes

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