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

HRID 2379028

Reaction equation

HRID 2379028 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 esterYield 89%

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 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-8540e583ed9e41bdb8570934ed3fa938
Source dataset
uspto-grants-1994_11
Patent number
US05360797

Linked notes

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