Triethyl phosphite → Diethyl 4-cyano-2-fluorobenzylphosphonate

HRID 1937142Notes

Reaction equation

HRID 1937142 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-e43729a42e7b45d297beb29ab22cafc4
Source dataset
uspto-grants-2002_05
Patent number
US06392082B1

Reaction notes

Loading…