Reaction #985284

ord-ae5cd8def3204b95beb38f585f862b91

Reaction equation

CCOP(=O)(OCC)c1ccc(-c2nc3c(N)c(F)cc(CCCCO)c3n2CC(C)C)o1
4-amino-7-(4-hydroxybutyl)-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole
c1ccc(P(c2ccccc2)c2ccccc2)cc1
PPh3
BrC(Br)(Br)Br
CBr4
CCOP(=O)(OCC)c1ccc(-c2nc3c(N)c(F)cc(CCCCBr)c3n2CC(C)C)o1
4-amino-7-(4-bromobutyl)-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherAfter 40 min. at rt solvent was removed

Procedure

To a cold (0° C.) solution of 1.0 mmol of 4-amino-7-(4-hydroxybutyl)-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole in 20 mL of CH2Cl2 was added 3.0 mmol of PPh3 and 3.0 mmol of CBr4. After 40 min. at rt solvent was removed and the residue was subjected to chromatography to give 4-amino-7-(4-bromobutyl)-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole. CCl4 gave the corresponding chloro compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07351399B2uspto-grants-2008_04