Triethyl phosphite → Diethyl [(4-benzoylphenyl)methyl]phosphonate

HRID 1728441Notes

Reaction equation

HRID 1728441 reaction equation
[C:1]([C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1)(=[O:8])[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]>>[CH2:17]([O:19][P:20]([CH2:13][C:12]1[CH:15]=[CH:16][C:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1)(=[O:24])[O:21][CH2:22][CH3:23])[CH3:18]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 1229514-(Bromomethyl)benzophenone

Product 1

HCID 56986843Diethyl [(4-benzoylphenyl)methyl]phosphonate

Conditions

Temperature
125 °C

Procedure

A mixture of 4.8 g of 4-benzoylbenzyl bromide and triethylphosphite was heated at 125° C. for 0.5 hours and cooled to room temperature. The resulting oil was purified by flash chromatography (70% ethyl acetate/hexanes) to afford 3.2 g of diethyl 4-benzoylbenzylphosphonic acid, as an oil. A mixture of 3.2 g (9.6 mmol) of diethyl 4-benzoylbenzylphosphonic acid and 40 ml of concentrated hydrochloric acid was refluxed for 7 hours and cooled to room temperature. The two phase mixture was partitioned between 125 ml of water and 400 ml of EtOAc, the EtOAc layer was dried over Na2SO4, filtered and evaporated to give 0.7 g of product; m.p. 172°-175° C.

Workup

  1. temperaturecooled to room temperature
  2. customThe resulting oil was purified by flash chromatography (70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9dfeb0201c4741eeb4ac34c0c58a09d5
Source dataset
uspto-grants-1994_07
Patent number
US05326905

Reaction notes

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