Acetone → 5-Bromo-6-methoxy-1-indanone

HRID 1063274Notes

Reaction equation

HRID 1063274 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[C:7](=[O:12])[CH2:6][CH2:5]2.[C:13](=O)([O-])[O-].[K+].[K+].IC.CC(C)=O>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:13])[C:7](=[O:12])[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 103313075-bromo-6-hydroxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 222787185-Bromo-6-methoxy-1-indanoneYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A round bottom flask, fitted with a stir bar and condenser was charged with 5-bromo-6-hydroxy-1-indanone (0.50 g, 2.20 mmol), potassium carbonate (0.456 g, 3.30 mmol), iodomethane (0.341 g, 2.40 mmol), and acetone (10 mL). After heating at reflux for 24 hours the mixture was diluted with ethyl acetate, washed with water (3×10 mL), brine (1×10 mL) and dried with MgSO4. The mixture was filtered and concentrated to give 0.382 g (72%) of 5-bromo-6-methoxyindan-1-one as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.73 (s, 1 H), 7.22 (s, 1 H), 3.95 (s, 3 H), 3.10 (m, 2 H), 2.73 (m, 2 H). MS (ESI+) for C10H9BrO2 m/z 239.9787 (M+H)+. Anal. Calcd. For C10H9BrO2: C, 49.82; H, 3.76. Found: C, 49.69; H, 3.72.

Workup

  1. customA round bottom flask, fitted with a stir bar and condenser
  2. temperatureAfter heating
  3. temperatureat reflux for 24 hours the mixture
  4. washwashed with water (3×10 mL), brine (1×10 mL)
  5. dry with materialdried with MgSO4
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5a75016ed1464917b5ab64a6eef11f76
Source dataset
uspto-grants-2005_11
Patent number
US06964965B2

Reaction notes

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