Potassium Carbonate → HCID 54558391, compound

HRID 2379375Notes

Reaction equation

HRID 2379375 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[CH2:16].COCCOCCN(CCOCCOC)CCOCCOC.C(=O)([O-])[O-].[K+].[K+]>[Pd](Cl)Cl.O.CN1C(=O)CCC1>[F:12][C:11]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[CH:16]=[CH:15][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 125074-MethoxystyreneHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 1361982-Bromo-5-nitrobenzotrifluoride

Product 1

HCID 54558391HCID 54558391, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 250 mL round bottom flask equipped with stirbar, reflux condenser and nitrogen inlet was placed 2-bromo-5-nitrobenzotrifluoride (5.40g, 20 mmol), 4-vinylanisole (2.95 g, 22 retool), NMP (20 mL), tris[2-(2-methoxyethoxy)ethyl]amine (TDA-1) (0.65 g, 2.0 mmol), potassium carbonate (4.2 g, 30 mmol) and palladium chloride (0.035 g, 0.20 retool). The resulting slurry was gradually warmed up to 140° and maintained at that temperature for 4 hr. The mixture was then cooled and water (200 mL) was added dropwise with stirring. The oily aqueous layer was decanted and replaced by more water (200 mL) and the resulting suspension was stirred and the black solid isolated by suction filtration, washed well with water and then air dried. The crude product was transferred to an Erlenmeyer flask containing Bentonite clay (5 g), silica gel (5 g) and methylcyclohexane (150 mL). The slurry was boiled with stirring, hot filtered and upon cooling the product was isolated from the filtrate as light yellow crystals, (3.30 g, 51%): mp 120.4-122.7°; 1H NMR (CDCl3)δ8.52 (s, 1H), 8.35 (d, J=9Hz, 1H), 7.94 (d, J=9 Hz), 7.51 (d, J=9 Hz, 2H), 7.28 (q, J=16 Hz, 2H), 6.95 (d, J=9 Hz), 3.86 (s, 3H); 13C NMR (CDCl3)ppm 160.669, 145.561,143.022, 136.361,128.812, 128.438, 128.005, 127.502, 127.251,126.439, 129.315, 121.961,121.864, 120.953. 119.581, 114.318, 55.278.

Workup

  1. customIn a 250 mL round bottom flask equipped with stirbar
  2. temperaturereflux condenser and nitrogen inlet
  3. temperatureThe resulting slurry was gradually warmed up to 140°
  4. temperaturemaintained at that temperature for 4 hr
  5. temperatureThe mixture was then cooled
  6. customThe oily aqueous layer was decanted
  7. stirringthe resulting suspension was stirred
  8. customthe black solid isolated by suction filtration
  9. washwashed well with water
  10. customair dried
  11. customThe crude product was transferred to an Erlenmeyer flask
  12. additioncontaining Bentonite clay (5 g), silica gel (5 g) and methylcyclohexane (150 mL)
  13. stirringwith stirring
  14. filtrationhot filtered
  15. temperatureupon cooling the product

Sources & evidence

ORD record
ord-839d9046911f44e7830a874d76f96700
Source dataset
uspto-grants-1994_11
Patent number
US05361148

Reaction notes

Loading…