Hydrochloric Acid → HCID 86707863, compound

HRID 922449Notes

Reaction equation

HRID 922449 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13])[CH:5]=[C:4]([F:14])[CH:3]=1.[CH:15]([O:17]CCO)=[CH2:16].C(=O)([O-])[O-].[K+].[K+].Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[F:14][C:4]1[CH:3]=[C:2]([C:15](=[O:17])[CH3:16])[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13])[CH:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 12995Hydroxyethyl vinyl etherHCID 81332359HCID 81332359, compound

Product 1

HCID 86707863HCID 86707863, compound

Reagents, catalysts & solvents 3

HCID 812191,3-Bis(diphenylphosphino)propaneCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

1-Bromo-3-fluoro-5-(3-methoxypropoxy)benzene (4.0 g) was added to water (30.4 mL), and then thereto were added ethylene glycol monovinyl ether (6.8 mL), potassium carbonate (2.52 g), 1,3-bis(diphenylphosphino)propane (125 mg) and palladium acetate (34 mg), and the mixture was heated to stir at 90° C. for 22 hours. After cooling, thereto was added concentrated hydrochloric acid (7.2 mL), and the mixture was stirred at room temperature for 20 minutes. The reaction solution was extracted with ethyl acetate, washed with saturated saline, and then dried over magnesium sulfate. After concentrating under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1→2/1) to give 1-[3-fluoro-5-(3-methoxypropoxy)phenyl]ethanone [REx(19-2)] (1.03 g) as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. stirringthe mixture was stirred at room temperature for 20 minutes
  4. extractionThe reaction solution was extracted with ethyl acetate
  5. washwashed with saturated saline
  6. dry with materialdried over magnesium sulfate
  7. concentrationAfter concentrating under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=20/1→2/1)

Sources & evidence

ORD record
ord-143af0cadb934bc8bedabe0d26b7da8b
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

Loading…