1-Naphthol → 1-Dichlorophosphoryloxynaphthalene

HRID 1359929Notes

Reaction equation

HRID 1359929 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[P:12](Cl)([Cl:15])([Cl:14])=[O:13].CCN(CC)CC>CCOCC>[P:12]([Cl:15])([Cl:14])([O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[O:13]

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 8471TriethylamineHCID 24813Phosphorus oxychloride

Product 1

HCID 5756311-Dichlorophosphoryloxynaphthalene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To 1-naphthol in Et2O (0.23 M) was added phosphorus oxychloride (1.0 eq.) and the solution was cooled to −78° C. Neat Et3N (1.0 eq) was added and the resulting solution was left to warm to RT overnight. The white slurry was filtered under an inert atmosphere and all volatiles were removed to yield the title compound as a colorless liquid that was used without further purification in the next step. 31P NMR (400 MHz, CDCl3): δ 3.93 ppm.

Workup

  1. waitthe resulting solution was left
  2. temperatureto warm to RT overnight
  3. filtrationThe white slurry was filtered under an inert atmosphere
  4. customall volatiles were removed

Sources & evidence

ORD record
ord-8811a46e97394e3f8534247de4bc141b
Source dataset
uspto-grants-2011_02
Patent number
US07879815B2

Reaction notes

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