Triethyl phosphite → Diethyl 4-cyano-2-fluorobenzylphosphonate

HRID 1766951Notes

Reaction equation

HRID 1766951 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 4-(bromomethyl)-3-fluorobenzonitrile (1.5 g, 7.0 mmol)[J. Med. Chem., 40, 2064 (1997)] and triethyl phosphite (1.4 g, 8.4 mmol) 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 the title compound (1.97 g, quantitative yield) 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-412b288457da462598dc9fcd676f9657
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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