Diethyl Ether → 3-(3-Bromophenyl)butan-2-one

HRID 1446387Notes

Reaction equation

HRID 1446387 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.CI.[C:14](=O)([O-])[O-].[Cs+].[Cs+].CCOCC>C(#N)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:14])[C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 27340931-(3-Bromophenyl)propan-2-one

Product 1

HCID 664367913-(3-Bromophenyl)butan-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-bromophenylacetone (4.7 g, 22 mmol) in acetonitrile (100 mL) was added methyl iodide (1.4 mL, 22 mmol) and cesium carbonate (14 g, 44 mmol). After stirring at room temperature for 17 h, the reaction mixture was poured into ether (100 mL) and water (100 mL). The organic layer was separated and the aqueous layer extracted with ether. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to dryness to give the title compound. 1H NMR (400 MHz, CD3OD): δ 7.45-7.40 (m, 2H), 7.3-7.2 (m, 2H), 3.87 (q, 1H), 2.06 (s, 3H), 1.34 (d, 3H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with ether
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0c13c44e1d374aa6979473ca6c543cb3
Source dataset
uspto-grants-2010_02
Patent number
US07667053B2

Reaction notes

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