Hydrochloric Acid → N-(5-bromo-4-fluoro-2-methylphenyl)acetamide

HRID 454501Notes

Reaction equation

HRID 454501 reaction equation
N1C=CC=CC=1.[C:7](Cl)(=[O:9])[CH3:8].[Br:11][C:12]1[C:13]([F:20])=[CH:14][C:15]([CH3:19])=[C:16]([CH:18]=1)[NH2:17].Cl>C(Cl)(Cl)Cl.O.C(Cl)Cl>[Br:11][C:12]1[C:13]([F:20])=[CH:14][C:15]([CH3:19])=[C:16]([NH:17][C:7](=[O:9])[CH3:8])[CH:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 27827865-Bromo-4-fluoro-2-methylaniline

Product 1

HCID 58508753N-(5-bromo-4-fluoro-2-methylphenyl)acetamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Pyridine (1.0 mL) and acetyl chloride (0.67 mL) were sequentially added to a methylene chloride (17 mL) solution of 5-bromo-4-fluoro-2-methylaniline (1.74 g), followed by stirring at room temperature for 1 hour. Water, 1 mol/L hydrochloric acid, and chloroform were added to the reaction mixture. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Hexane was added to the obtained residue, and the solid substance was collected by filtration to obtain 1.83 g of N-(5-bromo-4-fluoro-2-methylphenyl)acetamide as a white solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionHexane was added to the obtained residue
  6. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-a684c11cb09f489989532e861ee75496
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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