Allyl bromide → HCID 11745836, compound

HRID 345060Notes

Reaction equation

HRID 345060 reaction equation
[H-].[Na+].[OH:3][CH2:4][P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].[CH2:13](Br)[CH:14]=[CH2:15]>C(OCC)C>[CH2:15]([O:3][CH2:4][P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8])[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 76513Diethyl phosphonomethanol

Product 1

HCID 11745836HCID 11745836, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

To a hexane washed suspension of 60% sodium hydride (262mg, 6.5 mmol) in diethyl ether (10 ml) was added diethyl hydroxymethylphosphonate (lg, 5.95 mmol) and the reaction mixture stirred for 1 hour at 20° C. under nitrogen. Allyl bromide (0.94 g, 0.67 ml, 7.7 mmol) was then added dropwise and the reaction mixture stirred for 2 hours at 20° C. The solids were filtered off and the filtrate diluted with dichloromethane (30 ml). The solution was washed with water (2×30 ml), dried (MgSO4) and the solvent evaporated to give diethyl allyloxymethylphosphonate (0.85 g, 69%) as a clear liquid needing no further purification. νmax (film) 1260, 1030 and 960 cm-1 ; δH (CDCl3) 1.34(6H, t, J7.3 Hz, 2×CH3), 3.71(2H, d, J8.3 Hz, CH2P), 4.17(6H, m, 2×CH2CH3 +CH2OCH2P), 5.28(2H, m, CH2 =CH), 5.88(1H, m, CH2 =CH).

Workup

  1. washTo a hexane washed
  2. stirringthe reaction mixture stirred for 2 hours at 20° C
  3. filtrationThe solids were filtered off
  4. additionthe filtrate diluted with dichloromethane (30 ml)
  5. washThe solution was washed with water (2×30 ml)
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-df621c5a5758495284b9c5f99b537ca6
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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