Triethyl phosphite → Phosphonic acid, [(4-fluoro-3-phenoxyphenyl)methyl]-, diethyl ester

HRID 1194408Notes

Reaction equation

HRID 1194408 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:11]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:19][P:20]([O:24]CC)[O:21][CH2:22][CH3:23])[CH3:18]>>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:11][P:20](=[O:24])([O:21][CH2:22][CH3:23])[O:19][CH2:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 129227144-(Bromomethyl)-1-fluoro-2-phenoxybenzene

Product 1

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

Conditions

Temperature
140 °C

Procedure

To 6.4 g of 3-phenoxy-4-fluorobenzyl bromide was added 7 ml of triethylphosphite, and the mixture was stirred at 140° C. for seven hours. After cooling, 13.1 g of the reaction mixture was purified by column chromatography on silica gel (eluent: benzene) to give 6.3 g of diethyl 3-phenoxy-4-fluorobenzylphosphonate.

Workup

  1. temperatureAfter cooling
  2. custom13.1 g of the reaction mixture was purified by column chromatography on silica gel (eluent: benzene)

Sources & evidence

ORD record
ord-48485c68e50c43dcb72c2452dad15531
Source dataset
uspto-grants-1989_03
Patent number
US04814340

Reaction notes

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