Bromine → 3'-Acetamido-2-bromoacetophenone

HRID 1729854Notes

Reaction equation

HRID 1729854 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[NH:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2].[Br:14]Br>C(Cl)(Cl)Cl>[Br:14][CH2:2][C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[NH:7][C:8](=[O:10])[CH3:9])=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 3462023'-Acetamidoacetophenone

Product 1

HCID 124318473'-Acetamido-2-bromoacetophenone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 110.0 g. (0.62 mole) of 3'-acetylacetanilide in 2400 ml. of chloroform is added dropwise a solution of 33.0 ml. (102.9 g; 0.644 mole) of bromine in 240 ml. of chloroform. The solution is stirred one hour and the resultant precipitate is then filtered, washed with ether and dried. The solid is stirred in a large volume of water to give an oily precipitate which crystallizes on further stirring. The solid is filtered, washed with water and then 2-propanol. The dried product weighs 148.34 g., and is recrystallized from 2-propanol to give the product, melting point 108.5°-110°C. Analysis: Calcd. for C10H10BrNO2 : Calcd: C, 46.90; H, 3.94; Br, 31.20; N, 5.47. Found: C, 47.12; H, 3.94; Br, 31.21; N, 5.47.

Workup

  1. filtrationthe resultant precipitate is then filtered
  2. washwashed with ether
  3. customdried
  4. stirringThe solid is stirred in a large volume of water
  5. customto give an oily precipitate which
  6. customcrystallizes on further stirring
  7. filtrationThe solid is filtered
  8. washwashed with water
  9. custom, and is recrystallized from 2-propanol
  10. customto give the product, melting point 108.5°-110°C

Sources & evidence

ORD record
ord-00cdee947e324f25a9f810b3e2c6a366
Source dataset
uspto-grants-1976_11
Patent number
US03989835

Reaction notes

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