Diethyl phosphonomethanol → 2-Diethylphosphonomethyloxy-5-bromonitrobenzene

HRID 2297030Notes

Reaction equation

HRID 2297030 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Na].[CH2:13]([O:15][P:16]([CH2:21][OH:22])(=[O:20])[O:17][CH2:18][CH3:19])[CH3:14]>CN(C=O)C>[CH2:13]([O:15][P:16]([CH2:21][O:22][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])([O:17][CH2:18][CH3:19])=[O:20])[CH3:14]

Participants

5

Reactant 3

HCID 76513Diethyl phosphonomethanolHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 5360545Sodium

Product 1

HCID 539162862-Diethylphosphonomethyloxy-5-bromonitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-fluoro-5-bromonitrobenzene (1 mmole) in DMF (5 mL) was cooled to 0° C., and treated with a solution of freshly prepared sodium salt of diethylhydroxymethylphosphonate (1.2 mmole) in DMF (5 mL). The mixture was stirred at room temperature for 16 h. Evaporation, extraction and chromatography provided 2-diethylphosphonomethyloxy-5-bromonitrobenzene.

Workup

  1. customEvaporation, extraction and chromatography

Sources & evidence

ORD record
ord-9bfabf87e297465984abc36cf55e6e1b
Source dataset
uspto-grants-2002_12
Patent number
US06489476B1

Reaction notes

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