1,6-Dibromohexane → HCID 15067934, compound

HRID 1789164Notes

Reaction equation

HRID 1789164 reaction equation
C(OP(CP(OC(C)C)(=O)OC(C)C)(OC(C)C)=O)(C)C.[C:22]1([P:39]([O:45]C(C)C)(=[O:44])[O:40]C(C)C)([P:29]([O:35]C(C)C)(=[O:34])[O:30]C(C)C)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.BrCCCCCCBr.C(P(OC(C)C)(=O)OC(C)C)(P(OC(C)C)(=O)OC(C)C)CCCCCCC(P(OC(C)C)(=O)OC(C)C)P(OC(C)C)(=O)OC(C)C>C1(C)C=CC=CC=1>[C:22]1([P:39]([OH:45])(=[O:40])[OH:44])([P:29]([OH:34])(=[O:30])[OH:35])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 123681,6-DibromohexaneHCID 74266Tetraisopropyl methylenediphosphonateHCID 15067933HCID 15067933, compound2×HCID 19821549HCID 19821549, compound

Product 1

HCID 15067934HCID 15067934, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Using the same procedure as in Example I, tetraisopropyl methane diphosphonic acid was converted to tetraisopropyl cycloheptane-1,1-diphosphonate by reaction with 1,6-dibromohexane at 80° C. for 18 h. 31P NMR (toluene) indicated that the reaction solution contained a mixture of the desired tetraisopropyl cycloheptane-1,1-diphosphonate (25.3 ppm) and octaisopropyl octane-1,1,8,8-tetraphosphonate (22.1 ppm). The compounds were separated by chromatography (1:1 hexane:THF eluent) on silica gel, and the desired ester was hydrolyzed using 6N refluxing hydrochloric acid as in Example I.

Workup

  1. customThe compounds were separated by chromatography (1:1 hexane:THF eluent) on silica gel
  2. temperaturerefluxing hydrochloric acid as in Example I

Sources & evidence

ORD record
ord-4846f36cfef547aa941828cad3472d14
Source dataset
uspto-grants-1987_08
Patent number
US04687768

Reaction notes

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