Triethyl phosphite → O,O-diethyl 2-trifluoromethylphenyl(phenyl)methylphosphonate

HRID 1720853Notes

Reaction equation

HRID 1720853 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[CH:5](Br)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[P:19]([O:26]CC)([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]>>[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[CH:5]([P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 224164932-(Trifluoromethyl)benzhydryl bromide

Product 1

HCID 22416499O,O-diethyl 2-trifluoromethylphenyl(phenyl)methylphosphonate

Procedure

A solution of 2-(trifluoromethyl)benzhydryl bromide (25.2 g, 79.8 mmol) in triethyl phosphite (20.5 mL, 120 mmol), under N2, was heated at 155° C. for 16 hours. Excess triethyl phosphite was removed by distillation to give a yellow oil, 28.8 g. The crude product was chromatographed on a silica gel column. Elution with ethyl acetate/hexane (1:1) afforded analytically pure O,O-diethyl 2-trifluoromethylphenyl(phenyl)methylphosphonate as a pale yellow oil. 300 MHz 1H NMR (CDCl3): δ4.86 (d, 1H, J-26.18 Hz, PCH). MS: 373 (M+1).

Workup

  1. customExcess triethyl phosphite was removed by distillation
  2. customto give a yellow oil, 28.8 g
  3. customThe crude product was chromatographed on a silica gel column
  4. washElution with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-0354842edf93404f8204d2d9834a08e2
Source dataset
uspto-grants-1996_04
Patent number
US05508273

Reaction notes

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