Trimethyl phosphite → HCID 86749349, compound

HRID 233450Notes

Reaction equation

HRID 233450 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, 0.0015M) and trimethylphosphite (15 mL, 0.126M) 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, 0.00132M, 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-7cb7510904b04227b4b5d3ff60129d52
Source dataset
uspto-grants-1997_01
Patent number
US05593980

Reaction notes

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