Diethylphosphite → Tetrahydrofuran

HRID 1596832Notes

Reaction equation

HRID 1596832 reaction equation
[CH2:1]([O:3][P:4]([O-:8])[O:5][CH2:6][CH3:7])[CH3:2].CC(C)([O-])C.[Na+].[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][C:17]=1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][P:4](=[O:8])([O:5][CH2:6][CH3:7])[O:3][CH2:1][CH3:2])=[CH:18][C:17]=1[O:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1.[O:24]1[CH2:25][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 3

HCID 3780918DiethylphosphiteHCID 129227144-(Bromomethyl)-1-fluoro-2-phenoxybenzeneHCID 23676156Sodium t-butoxide

Product 2

HCID 8028TetrahydrofuranYield 98%HCID 11279166Phosphonic acid, [(4-fluoro-3-phenoxyphenyl)methyl]-, diethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of diethylphosphite (6.9 g, 0.05 mol) in tetrahydrofuran is cooled to 10° C., treated portionwise with sodium t-butoxide (4.9 g, 0.05 mol) while maintaining the reaction mixture temperature below about 20° C., stirred at room temperature for 5 minutes, cooled, and treated dropwise with 4-fluoro-3-phenoxybenzyl bromide (14.05 g, 0.05 mol) at about 10-15° C. to give a solution of the title product in tetrahydrofuran (98% yield by gas chromatography).

Workup

  1. temperaturewhile maintaining the reaction mixture temperature below about 20° C.
  2. temperaturecooled

Sources & evidence

ORD record
ord-15ba6dbb694244ddb3175ac9f194cd25
Source dataset
uspto-grants-2001_09
Patent number
US06291721B1

Reaction notes

Loading…