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

HRID 510854Notes

Reaction equation

HRID 510854 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 g, 54 mmol, from Aldrich) in acetic acid (100 mL) was added N-bromosuccinimide (12 g, 65 mmol) and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo, neutralized with saturated sodium bicarbonate and filtered to remove insoluble succinimide. The filtrate was 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 recrystallized from a mixture of ethyl acetate and hexane (11.4 g, 80%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationfiltered
  3. customto remove insoluble succinimide
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe crude product was recrystallized from a mixture of ethyl acetate and hexane (11.4 g, 80%)

Sources & evidence

ORD record
ord-05fae7721413497d9c6d63a2fdf94e71
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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