Triethyl phosphite → Diethyl 4-cyano-2-fluorobenzylphosphonate

HRID 1936839Notes

Reaction equation

HRID 1936839 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[F:11].[P:12]([O:19]CC)([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH2:2][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])=[C:4]([F:11])[CH:5]=1)#[N:8]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 27831494-(Bromomethyl)-3-fluorobenzonitrile

Product 1

HCID 10967607Diethyl 4-cyano-2-fluorobenzylphosphonateYield 103.8%

Conditions

Temperature
150 °C

Procedure

A mixture of 1.5 g (7.0 mmol) of 4-(bromomethyl)-3-fluorobenzonitrile [ref J.Med.Chem., 40, 2064 (1997)] and 1.4 g (8.4 mmol) of triethyl phosphite was heated at 150° C. for 2 hours. At the end of this time, the reaction mixture was concentrated under reduced pressure. Volatile materials in the residue thus obtained were removed by heating said residue at 100° C. in vacuo for 1 hour to afford 1.97 g (quantitative yield) of the title compound as an oil which solidified in the freezer. This oily product was used in the next step without further purification.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated under reduced pressure
  2. customVolatile materials in the residue thus obtained
  3. customwere removed
  4. temperatureby heating
  5. customat 100° C.
  6. customfor 1 hour

Sources & evidence

ORD record
ord-9cd11bb5299b43298e4f1f187676ad57
Source dataset
uspto-grants-2002_05
Patent number
US06391903B1

Reaction notes

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