Hydrochloric Acid → HCID 67330889, compound

HRID 1942474Notes

Reaction equation

HRID 1942474 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.[OH-].[Na+].[O:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.Cl.[O:22]1CCC[CH2:23]1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][C:17]3([CH2:18][CH2:19][O:14][CH2:15][CH2:16]3)[C:23](=[O:22])[NH:9][C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 243644-Bromo-2-nitrophenolHCID 121599Tetrahydro-4H-pyran-4-one

Product 1

HCID 67330889HCID 67330889, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-bromo-2-nitrophenol (5.0 g) in tetrahydrofuran (80 ml) was added sodium hydroxide powder (7.8 g), and the mixture was stirred at room temperature for 15 minutes, and further thereto was added tetrahydro-4H-pyran-4-one (180 ml). Under ice-cooling, chloroform (7.3 ml) was added thereto dropwise, and the mixture was stirred for one hour. Then, the mixture was further stirred at room temperature overnight. To the reaction mixture was added 2N hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. Using the obtained residue, the title compound (1.6 g) was obtained in a similar manner to Reference Example 2.

Workup

  1. temperatureUnder ice-cooling
  2. stirringdropwise, and the mixture was stirred for one hour
  3. stirringThen, the mixture was further stirred at room temperature overnight
  4. extractionthe mixture was extracted with chloroform
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-32f3d784c6af45ecb8e56fef8e975ffc
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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