Triethylamine → HCID 178454800, compound

HRID 1292573Notes

Reaction equation

HRID 1292573 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[CH3:9][P:10]([O-:16])[O:11][CH2:12][CH:13]([CH3:15])[CH3:14].C(N(CC)CC)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:9][PH:10](=[O:16])[O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 99931-Bromo-4-fluorobenzeneHCID 86741778Isobutyl methanephosphonite

Product 1

HCID 178454800HCID 178454800, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 11776TriphenylphosphineCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 50.0 g (289 mmol) of 4-bromofluorobenzene, 43.3 g (318 mmol) of isobutyl methanephosphonite, 43.8 ml (318 mmol) of triethylamine, 1.64 g (0.29 mmol,1 mol %) of bis(dibenzylideneacetone)-palladium and 1.50 g (0.58 mmol, 2 mol %) of triphenylphosphine was heated for 20 hours at 100° C. under an inert gas atmosphere. At 23° C., the solution was filtered off from the ammonium salt formed and the filtrate was evaporated under reduced pressure. Fractional distillation under reduced pressure gave 54.60 g (83% of theory) of isobutyl 4-fluorophenylmethylphosphinate having a boiling point of 83° C./0.08 mbar.

Workup

  1. filtrationAt 23° C., the solution was filtered off from the ammonium salt
  2. customformed
  3. customthe filtrate was evaporated under reduced pressure
  4. distillationFractional distillation under reduced pressure

Sources & evidence

ORD record
ord-e6f2a48747eb4053b2d23e3f6f939382
Source dataset
uspto-grants-1998_05
Patent number
US05756804

Reaction notes

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