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

HRID 2274109Notes

Reaction equation

HRID 2274109 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, from Aldrich) in acetic acid (100 mL) was added N-bromosuccinimide (11.6 g, 65.0 mmol) and the resulting mixture was stirred at rt for 18 h. The reaction mixture was concentrated in vacuo, then neutralized with sat. sodium bicarbonate, and the insoluble succinimide was removed by filtration. The filtrate was extracted with ethyl acetate (EtOAc). 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 EtOAc and hexane (11.4 g, 80%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe insoluble succinimide was removed by filtration
  3. extractionThe filtrate was extracted with ethyl acetate (EtOAc)
  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 recrystallized from a mixture of EtOAc and hexane (11.4 g, 80%)

Sources & evidence

ORD record
ord-e1b84c20e4c7480ea142baa91f8ef05f
Source dataset
uspto-grants-2015_09
Patent number
US09126948B2

Reaction notes

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