Hydrochloric Acid → HCID 67228021, compound

HRID 573071Notes

Reaction equation

HRID 573071 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.Cl>CN(C)C=O>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([F:1])=[CH:3][C:4]=1[O:12][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 2775386Methyl 4-fluorosalicylate

Product 1

HCID 67228021HCID 67228021, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-fluoro-2-hydroxybenzoate (1661 mg) was added to N,N-dimethylformamide (50 mL). Sodium hydride (60% in mineral oil, 430 mg) was added, the solution stirred for 15 minutes at room temperature, and 1-(bromomethyl)-4-methoxybenzene (2061 mg) was added. The solution was stirred at room temperature for three days, added to 0.01M aqueous HCl, and extracted with ethyl acetate. The organic phase was washed with water twice, washed with brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed under vacuum.

Workup

  1. stirringThe solution was stirred at room temperature for three days
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water twice
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-9fb4271309b545bbb35f4f083e7ba7ab
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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