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

HRID 2379028

Reaktionsgleichung

Reaktionsgleichung von HRID 2379028
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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 86747693[2-Fluoro-1,3-phenylenebis(methylene)]bisphosphonic acid tetramethyl esterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8540e583ed9e41bdb8570934ed3fa938
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05360797

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