Diethyl methylphosphonite → Ethyl [3-(4-bromophenyl)-3-oxopropyl]methylphosphinate

HRID 1013540Notes

Reaction equation

HRID 1013540 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH2:9][CH2:10]Cl)=[CH:4][CH:3]=1.[CH3:13][P:14]([O:18]CC)[O:15][CH2:16][CH3:17]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH2:9][CH2:10][P:14]([CH3:13])(=[O:18])[O:15][CH2:16][CH3:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 85063Diethyl methylphosphoniteHCID 957904'-Bromo-3-chloropropiophenone

Product 1

HCID 57925852Ethyl [3-(4-bromophenyl)-3-oxopropyl]methylphosphinate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(4-bromophenyl)-3-chloropropan-1-one (4.5 g, 18.18 mmol) and diethyl methylphosphonite (6 g, 44.1 mmol) were stirred in refluxing toluene (9 mL) for 5 hours. Room temperature was attained and the solvent removed in vacuo. Purification of the residue by MPLC (0-10% MeOH-EtOAc) gave ethyl [3-(4-bromophenyl)-3-oxopropyl]methylphosphinate as a pale yellow oil that crystallised on standing.

Workup

  1. customRoom temperature
  2. customthe solvent removed in vacuo
  3. customPurification of the residue by MPLC (0-10% MeOH-EtOAc)

Sources & evidence

ORD record
ord-8fd73d4efa7d407796e5add8d870aebc
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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