N-bromobutanimide → HCID 86666897, compound

HRID 510983Notes

Reaction equation

HRID 510983 reaction equation
[Cl:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([OH:12])=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:7]=1.[Br:14]N1C(=O)CCC1=O>C(O)(=O)C>[Br:14][C:4]1[C:5]([OH:12])=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:7]=[C:2]([Cl:1])[C:3]=1[CH3:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 242119961-(5-Chloro-2-hydroxy-4-methylphenyl)propan-1-one

Product 1

HCID 86666897HCID 86666897, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

The 1-(5-chloro-2-hydroxy-4-methylphenyl)propan-1-one (1.6 g, 8.0 mmol) was dissolved in acetic acid (20.0 mL) and N-bromosuccinimide (1.7 g, 9.7 mmol) was added. The reaction was warmed in an oil bath to 65° C. and monitored by LC/MS. After heating for 3 h the reaction was complete. This was allowed to cool to room temperature and was concentrated in vacuo. The residue was diluted with EtOAc and washed with water (twice), brine, dried over magnesium sulfate and concentrated to give 1-(3-bromo-5-chloro-2-hydroxy-4-methylphenyl)propan-1-one as an amber oil. This oil was dissolved in DMF (10.0 mL) and potassium carbonate (3.3 g, 24 mmol) and methyl iodide (0.75 mL, 12 mmol) were added. The reaction was stirred at 65° C. for 18 hours. The reaction was complete, and the reaction mixture was diluted with EtOAc, washed with water, brine, dried over magnesium sulfate and concentrated to give the crude product as a dark oil. The product was purified by chromatography on silica gel eluting with a hexane: EtOAc gradient to give 1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)propan-1-one as an oil (1.8 g, 81%). LCMS calculated for C11H13BrClO2 (M+H)+: m/z=290.9, 292.9. found: 290.8, 292.9.

Workup

  1. temperatureAfter heating for 3 h the reaction
  2. temperatureto cool to room temperature
  3. concentrationwas concentrated in vacuo
  4. additionThe residue was diluted with EtOAc
  5. washwashed with water (twice), brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f46a2619b5a4445da3998a3f4b2f594a
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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