Dimethylformamide → HCID 68502637, compound

HRID 922435Notes

Reaction equation

HRID 922435 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].CN(C)[CH:14]=[O:15].[C:17](=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][O:27][CH3:28].[C:29](#N)[CH3:30]>O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:24][CH2:25][CH2:26][O:27][CH3:28])=[O:7])=[CH:4][C:3]=1[O:11][CH2:17][CH2:29][CH2:30][O:15][CH3:14]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 5245511-Bromo-3-methoxypropaneHCID 5936354-Fluoro-3-hydroxybenzoic acid

Product 1

HCID 68502637HCID 68502637, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of 4-fluoro-3-hydroxybenzoic acid (2.0 g) in acetonitrile (100 mL)-N,N-dimethylformamide (50 mL)-water (2.0 mL) were added potassium carbonate (5.31 g) and 1-bromo-3-methoxypropane (4.32 g), and the mixture was heated to reflux at 90° C. for 18 hours. To the reaction mixture was added water under ice-cooling, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1→1/2 to give 3-methoxypropyl 4-fluoro-3-(3-methoxypropoxy)benzoate [REx(2-1)] (2.72 g) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-c3476ac4113a408c88e93baea6ecea8e
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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