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

HRID 2104285Notes

Reaction equation

HRID 2104285 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-07b8085e59a5466fb5a68cba4f838671
Source dataset
uspto-grants-2009_08
Patent number
US07576239B2

Reaction notes

Loading…