N-bromobutanimide → 1-(3-Bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone

HRID 1192586Notes

Reaction equation

HRID 1192586 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[Br:13]N1C(=O)CCC1=O>C(O)(=O)C>[Br:13][C:4]1[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[CH3:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 5982295'-Chloro-2'-hydroxy-4'-methylacetophenone

Product 1

HCID 120274791-(3-Bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 1-(5-chloro-2-hydroxy-4-methylphenyl)ethanone (10.0 g, 54.2 mmol) in acetic acid (100 mL) was added N-bromosuccinimide (11.6 g, 65.0 mmol) and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo, then neutralized with sat. sodium bicarbonate, insoluble succinimide filtered off and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and then concentrated to dryness under reduced pressure. The crude product was recrystalized from a mixture of ethyl acetate and hexane (11.42 g, 80%). 1H NMR (CDCl3, 300 MHz) δ 12.96 (1H, s), 7.72 (1H, s), 2.64 (3H, s), 2.59 (3H, s) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationfiltered off
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe crude product was recrystalized from a mixture of ethyl acetate and hexane (11.42 g, 80%)

Sources & evidence

ORD record
ord-25912acac96b407e9049a6442206c84f
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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