Triethylamine → Diethyl 4-(amino(phenyl)methyl)phenylphosphonate

HRID 1525210Notes

Reaction equation

HRID 1525210 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH2:9])=[CH:4][CH:3]=1.[P:16]([O-:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19].CCN(CC)CC>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:9][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5]1[CH:6]=[CH:7][C:2]([P:16](=[O:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 350040(4-Bromophenyl)(phenyl)methanamineHCID 3780918Diethylphosphite

Product 1

HCID 89462707Diethyl 4-(amino(phenyl)methyl)phenylphosphonate

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Procedure

To 2-b′ (9 g, 25 mmol), diethyl phosphite (10.5 g, 75 mmol) and Et3N (8.5 g, 75 mmol) in toluene was added PdCl2(dppf) (7.5 g). The mixture was allowed to stir overnight at reflux. The mixture was filtered and the filtrate was concentrated under vacuum. The residue was taken into ethyl acetate and washed with saturated NH3Cl. The organic layer was concentrated under vacuum and the residue was purified over silica gel to provide the crude product 2-c (15 g). (M+Na)+=442.

Workup

  1. temperatureat reflux
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. washwashed with saturated NH3Cl
  5. concentrationThe organic layer was concentrated under vacuum
  6. customthe residue was purified over silica gel

Sources & evidence

ORD record
ord-ff9f84fb57a74a3492ba554561281064
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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