Hydrochloric Acid → 4'-Bromoacetanilide

HRID 1582848Notes

Reaction equation

HRID 1582848 reaction equation
Br([O-])(=O)=O.[Na+].[Br:6]Br.[C:8]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:10])[CH3:9].Cl>O.ClCCl.BrBr>[Br:6][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:8](=[O:10])[CH3:9])=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 904AcetanilideHCID 24408BromineHCID 23668195Sodium Bromate

Product 1

HCID 76834'-BromoacetanilideYield 92.7%

Reagents, catalysts & solvents 3

HCID 24408BromineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4.3 ml of alkaline (lime) bromine (containing 0.242 g bromide and 0.051 g bromate per ml of solution) and 0.52 g sodium bromate in 10 ml water were taken in a round bottom flask with total bromine content of 19.135 mmol. Into this was added 2.5 g (18.517 mmol) of acetanilide in 12.5 ml dichloromethane. 25 ml of 3.6 N hydrochloric acid was added over a period of 13 min under stirring at room temperature. Stirring was continued for another 30 min. The precipitate was filtered, washed with water and dried to give 3.689 g (92.7%) of p-bromoacetanilide (m.p. 164-168° C.) characterized through spectroscopic techniques.

Workup

  1. stirringStirring
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ee869ab7c6254ebd96bf7a1b4515a6df
Source dataset
uspto-grants-2004_05
Patent number
US06740253B2

Reaction notes

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