Trimethyl phosphite → HCID 53693742, compound

HRID 2379027Notes

Reaction equation

HRID 2379027 reaction equation
Br[CH2:2][C:3]1[C:12]([CH2:13]Br)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.C[O:16][P:17]([O:20][CH3:21])[O:18][CH3:19]>C1(C)C=CC=CC=1>[CH3:19][O:18][P:17]([CH2:2][C:3]1[C:12]([CH2:13][P:17](=[O:16])([O:20][CH3:21])[O:18][CH3:19])=[CH:11][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:16])[O:20][CH3:21]

Participants

4

Reactant 2

HCID 8472Trimethyl phosphiteHCID 2622592,3-Bis(bromomethyl)naphthalene

Product 1

HCID 53693742HCID 53693742, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A flask is charged with 2,3-bis(bromomethyl)naphthalene (Example 22(b), 2.80 g, 8.9 mmol) and toluene (50 mL). The solution is heated at reflux and 25 mL of the toluene is collected in a Dean-Stark trap. The solution is then cooled to room temperature and trimethylphosphite (4.0 mL, 0.034 mol) is added. The reaction is heated to reflux temperature for 24 hours. The excess trimethylphosphite and toluene are removed at reduced pressure, giving a white solid (3.24 g). The solid is recrystallized from ethyl acetate-hexane to give 2.55 g of white crystals, mp 119.5°-120.5° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux
  3. custom25 mL of the toluene is collected in a Dean-Stark trap
  4. temperatureThe reaction is heated
  5. temperatureto reflux temperature for 24 hours
  6. customThe excess trimethylphosphite and toluene are removed at reduced pressure

Sources & evidence

ORD record
ord-0fb972fbf37649cea934837c7452b477
Source dataset
uspto-grants-1994_11
Patent number
US05360797

Reaction notes

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