Triethylamine → Ethyl 2-(3-(diethoxyphosphoryl)phenyl)acetate

HRID 1525326Notes

Reaction equation

HRID 1525326 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=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:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1)([O:18][CH2:19][CH3:20])=[O:21])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3780918DiethylphosphiteHCID 11470552Ethyl 3-(bromophenyl)acetate2×

Product 1

HCID 89462900Ethyl 2-(3-(diethoxyphosphoryl)phenyl)acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of ethyl 2-(3-bromophenyl)acetate, 35i-b, (22.1 g, 90 mmol), diethylphosphite (25.1 g, 180 mmol) and triethylamine (27.5 g, 270 mmol) in toluene (300 mL) was added [1,1′-bis(diphenylphosphino) ferrocene]dicholoropalladium (3 g). The mixture was allowed to stir overnight at 110° C. and was filtered. The solution was concentrated to afford the crude product which was purified by column chromatography to give the title compound, 35i-c as yellow brown oil (26 g, crude). 1H NMR (300 MHz, CDCl3): δ 1.20-1.32 (m, 9H), 3.62 (s, 2H), 4.00-4.16 (m, 6H), 7.36-7.47 (m, 2H), 7.64-7.71 (m, 2H). LC-MS (M+H)+ 301.

Workup

  1. filtrationwas filtered
  2. concentrationThe solution was concentrated
  3. customto afford the crude product which
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-cd65b4fa07f841df917e248418cd21e5
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

Loading…