1,2-Dimethoxyethane → HCID 57597488, compound

HRID 1786707Notes

Reaction equation

HRID 1786707 reaction equation
C([C:3]1[C:4](Br)=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])C.[C:13]([C:16]1[CH:17]=[C:18](OB(O)O)[CH:19]=[CH:20][CH:21]=1)(=[O:15])[CH3:14].C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].[CH2:37]([CH2:40]OC)OC>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[CH2:37]([O:8][C:6]([C:5]1[C:9]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([C:13](=[O:15])[CH3:14])[CH:17]=2)=[CH:10][CH:11]=[CH:3][CH:4]=1)=[O:7])[CH3:40]

Participants

8

Reactant 5

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 23030395HCID 23030395, compoundHCID 230304032-Bromo-3-ethylbenzoic acid

Product 1

HCID 57597488HCID 57597488, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of ethyl 2-bromobenzoic acid (10.0 g) and 3-acetylphenylboric acid (7.87 g) in dimethoxyethane (200 ml) was added 2 N sodium carbonate solution (50 ml), and the mixture was deaerated and argon-substituted. To this mixture was added tetrakis(triphenylphosphine) palladium (0) (5.04 g), and the mixture was heated to reflux for 15 hours. The obtained reaction mixture was subjected to cooling, and distributed between ethyl acetate (400 ml) and saturated sodium bicarbonate solution (400 ml). The aqueous layer was further extracted with ethyl acetate (200 ml), and the combined organic layer was washed with saturated brine, dried with magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography to give the title compound as a yellow oil (11.08 g, 95%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 15 hours
  3. customThe obtained reaction mixture
  4. temperatureto cooling
  5. extractionThe aqueous layer was further extracted with ethyl acetate (200 ml)
  6. washthe combined organic layer was washed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-dbbb1c6c81804f80891a6abbf08e6b2f
Source dataset
uspto-grants-2009_03
Patent number
US07507753B2

Reaction notes

Loading…