Trimethyl phosphite → HCID 23208053, compound

HRID 1440666Notes

Reaction equation

HRID 1440666 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[CH3:10][O:11][P:12]([O:15]C)[O:13][CH3:14]>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][P:12](=[O:15])([O:13][CH3:14])[O:11][CH3:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 680214-Fluorobenzyl bromide

Product 1

HCID 23208053HCID 23208053, compound

Procedure

A mixture of 4-fluorobenzyl bromide (4.86 g, 0.026 M) and trimethylphosphite (10 mL, 0.085 M) is heated at the reflux temperature for 48 hours. The solution is cooled and excess trimethylphosphite is removed under reduced pressure. The crude product is chromatographed over silica gel (40-63 mμ, 400 g, 45 mL fractions, ethyl acetate), eluting with ethyl acetate. Fractions 41-80 are combined, concentrated, and placed under vacuum for 36 hours. The product (4.52 g) is a colorless oil.

Workup

  1. temperatureis heated at the reflux temperature for 48 hours
  2. temperatureThe solution is cooled
  3. customexcess trimethylphosphite is removed under reduced pressure
  4. customThe crude product is chromatographed over silica gel (40-63 mμ, 400 g, 45 mL fractions, ethyl acetate)
  5. washeluting with ethyl acetate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-55ea123b8ed646c3a8ebfb38c2526a86
Source dataset
uspto-grants-1996_03
Patent number
US05500417

Reaction notes

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