Trimethyl phosphite → [2-Fluoro-1,3-phenylenebis(methylene)]bisphosphonic acid tetramethyl ester

HRID 487889

Reaction equation

HRID 487889 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9]Br)[C:4]=1[F:11].C[O:13][P:14]([O:17][CH3:18])[O:15][CH3:16]>C1(C)C=CC=CC=1>[CH3:16][O:15][P:14]([CH2:2][C:3]1[C:4]([F:11])=[C:5]([CH2:9][P:14](=[O:13])([O:17][CH3:18])[O:15][CH3:16])[CH:6]=[CH:7][CH:8]=1)(=[O:13])[O:17][CH3:18]

Participants

4

Reactant 2

HCID 8472Trimethyl phosphiteHCID 27360031,3-Bis(bromomethyl)-2-fluorobenzene

Product 1

HCID 86747693[2-Fluoro-1,3-phenylenebis(methylene)]bisphosphonic acid tetramethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,6-bis(bromomethyl)-1-fluorobenzene (2.82 g, 0.010 mole) and trimethylphosphite (5.0 mL, 0.042 mole) in toluene (25 mL) is heated at reflux temperature for 24 hours, after which the solvent and excess trimethylphosphite are removed under reduced pressure. The solid residue is crystallized from ethyl acetate-hexane, giving 3.12 g (0.0089 mole, 89%) of of the title compound, mp 116.5°-117.5° C. Recrystallization gives 2.64 g, mp 117°-118° C.

Workup

  1. temperatureat reflux temperature for 24 hours
  2. customafter which the solvent and excess trimethylphosphite are removed under reduced pressure
  3. customThe solid residue is crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-fd7c419735424e3d905e0ec459d98bd1
Source dataset
uspto-grants-1994_03
Patent number
US05298498

Linked notes

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