Triethylamine → Methyl 2-(4-(diethoxyphosphoryl)phenyl)propanoate

HRID 1525227Notes

Reaction equation

HRID 1525227 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH2:14]([O:16][P:17]([O-:21])[O:18][CH2:19][CH3:20])[CH3:15].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:14]([O:16][P:17]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1)([O:18][CH2:19][CH3:20])=[O:21])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 11032083Methyl 2-(4-bromophenyl)propanoate2×

Product 1

HCID 89464879Methyl 2-(4-(diethoxyphosphoryl)phenyl)propanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of methyl 2-(4-bromophenyl)propanoate, 7-e, (500 mg, 2.06 mmol), diethylphosphite (994 mg, 7.20 mmol) and triethylamine (681 mg, 6.7 mmol) in toluene (5 mL) was added [1,1′-bis(diphenylphosphino) ferrocene]dicholoropalladium (54 mg). The resulting reaction mixture was heated at 110° C. under nitrogen overnight. The cooled reaction mixture was filtrated (washed with DCM, 3×10 mL), and the filtrate was concentrated to afford the crude product which was purified by column chromatography to give the title compound, 7-f, as yellow brown oil (500 mg, 99%). 1H NMR (300 MHz, CDCl3) δ1.30-1.39 (m, 6H), 1.51 (d, J=7.2 Hz, 3H), 3.67 (s, 3H), 3.77 (q, J=7.2 Hz, 1H), 4.05-4.20 (m, 4H), 7.37-7.41 (m, 2H), 7.72-7.79 (m, 2H). LC-MS (M+H)+ 301.

Workup

  1. customThe resulting reaction mixture
  2. customThe cooled reaction mixture
  3. filtrationwas filtrated
  4. wash(washed with DCM, 3×10 mL)
  5. concentrationthe filtrate was concentrated
  6. customto afford the crude product which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-9c131ea002f14e71b5b3794e31a4739e
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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