Triphenylphosphine → (3,5-Dichloro-4-formylphenoxymethyl)-phosphonic acid diethyl ester

HRID 1515022Notes

Reaction equation

HRID 1515022 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].[CH2:12]([O:14][P:15]([CH2:20]O)(=[O:19])[O:16][CH2:17][CH3:18])[CH3:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:12]([O:14][P:15]([CH2:20][O:10][C:8]1[CH:9]=[C:2]([Cl:1])[C:3]([CH:4]=[O:5])=[C:6]([Cl:11])[CH:7]=1)(=[O:19])[O:16][CH2:17][CH3:18])[CH3:13]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 76513Diethyl phosphonomethanolHCID 5283822,6-Dichloro-4-hydroxybenzaldehydeHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 86651275(3,5-Dichloro-4-formylphenoxymethyl)-phosphonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-dichloro-4-hydroxy-benzaldehyde (190 mg, 1.0 mmol) and hydroxymethyl-phosphonic acid diethyl ester (278 mg, 1.0 mmol) in THF (8 mL) was added PPh3-resin (553 mg, 2.13 mmol/g) and DEAD (0.54 ml of 40% solution, 1.2 mmol). The suspension was stirred at ambient temperature overnight then the reaction mixture was filtered and partioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were dried with MgSO4, filtered and concentrated. Purification by flash chromatography using heptane/EtOAc (1:3) gave (3,5-dichloro-4-formylphenoxymethyl)-phosphonic acid diethyl ester as a colorless oil.

Workup

  1. filtrationthe reaction mixture was filtered
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-4463308995ac4112a22328deebbfabf9
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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