N-Bromoacetamide → Sodium (2-hydroxy-1-bromopropyl)-phosphonate

HRID 267564

Reaction equation

HRID 267564 reaction equation
[CH:1](/[P:4](=[O:7])([OH:6])[OH:5])=[CH:2]/[CH3:3].[OH-:8].[Na+:9].[Br:10]NC(=O)C>O>[OH:8][CH:2]([CH3:3])[CH:1]([P:4](=[O:6])([O-:5])[O-:7])[Br:10].[Na+:9].[Na+:9]

Participants

5

Reactant 3

HCID 4353N-Bromoacetamide2×HCID 14798Sodium HydroxideHCID 6436667P-(1Z)-1-Propen-1-ylphosphonic acid

Product 1

HCID 86733120Sodium (2-hydroxy-1-bromopropyl)-phosphonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.8 g. of cis-propenylphosphonic acid is dissolved in 50 ml. of water and the pH of the solution is adjusted to 4.2 by the addition of 2.5 N sodium hydroxide. 13.8 g. of N-bromoacetamide is added and the suspension is stirred at room temperature. The reaction is complete when the N-bromoacetamide is in solution and the mixture is negative to starch-iodide paper. The solution is lyophilized and the residue is triturated several times with chloroform to give sodium (2-hydroxy-1-bromopropyl)-phosphonate.

Workup

  1. customthe residue is triturated several times with chloroform

Sources & evidence

ORD record
ord-d3df9ff839424b4a863354e31b5ebf93
Source dataset
uspto-grants-1976_03
Patent number
US03943153

Linked notes

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