Hydrochloric Acid → 4-Bromo-2-chloro-N-(2-oxoethyl)benzamide

HRID 394855Notes

Reaction equation

HRID 394855 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][CH2:9][CH:10](OCC)[O:11]CC)=[O:7])=[C:4]([Cl:19])[CH:3]=1.Cl.O>C1COCC1>[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][CH2:9][CH:10]=[O:11])=[O:7])=[C:4]([Cl:19])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 223137884-bromo-2-chloro-N-(2,2-diethoxyethyl)benzamide

Product 1

HCID 223137814-Bromo-2-chloro-N-(2-oxoethyl)benzamideYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2-chloro-N-(2,2-diethoxyethyl)benzamide (14.88 g, 42.44 mmol) in THF (50 mL) was added 2N HCl (50 mL) at room temperature. After 24 hours, water (100 mL) was added to the mixture, then the mixture was extracted with ethyl acetate (100 mL×2), the organic layer was washed with water (50 mL), dried over MgSO4. Removal of the solvent, gave a title compound (6.98 g, 60% yield).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (100 mL×2)
  2. washthe organic layer was washed with water (50 mL)
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-994529cf00af43f8a4de1e002695a03b
Source dataset
uspto-grants-2003_08
Patent number
US06603008B1

Reaction notes

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