Trimethyl phosphite → HCID 86749349, compound

HRID 1440675Notes

Reaction equation

HRID 1440675 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Br)=[CH:5][C:4]=1[CH2:11]Br.C[O:14][P:15]([O:18][CH3:19])[O:16][CH3:17]>C1(C)C=CC=CC=1>[C:3]1([CH2:2][P:15](=[O:14])([O:18][CH3:19])[O:16][CH3:17])[CH:8]=[CH:7][C:6]([CH2:9][P:15](=[O:14])([O:18][CH3:19])[O:16][CH3:17])=[CH:5][C:4]=1[CH2:11][P:15](=[O:14])([O:18][CH3:19])[O:16][CH3:17]

Participants

4

Reactant 2

HCID 8472Trimethyl phosphiteHCID 104283861,2,4-tris(bromomethyl)benzene

Product 1

HCID 86749349HCID 86749349, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1,2,4-tris(bromomethyl)benzene (Preparation 4, 0.532 g, 0.0015 M) and trimethylphosphite (15 mL, 0.126 M) in dry toluene (25 mL) is stirred and heated at reflux temperature for 80 hours. Solvent and excess trimethylphosphite are removed under reduced pressure and the oily residue is chromatographed over silica gel (50 g, 40-63 μm, 10% CH3OH--CHCl3, 8 mL fractions) using 10% CH3OH--CHCl3 to elute the column. Fractions 16-22 contain the title compound (0.587 g, 0.00132 M, 88%), which is a viscous oil.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 80 hours
  3. customSolvent and excess trimethylphosphite are removed under reduced pressure
  4. customthe oily residue is chromatographed over silica gel (50 g, 40-63 μm, 10% CH3OH--CHCl3, 8 mL fractions)
  5. washCHCl3 to elute the column

Sources & evidence

ORD record
ord-bf25cbdfb8094d84b1accc6345a6da13
Source dataset
uspto-grants-1996_03
Patent number
US05500417

Reaction notes

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