Water → (2-Bromo-4-methoxy-phenyl)-(4-ethyl-phenyl)-methanone

HRID 1359911Notes

Reaction equation

HRID 1359911 reaction equation
[CH3:1][O-:2].[Na+].[Br:4][C:5]1[CH:10]=[C:9](F)[CH:8]=[CH:7][C:6]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][CH:15]=1)=[O:13].O>CN(C=O)C>[Br:4][C:5]1[CH:10]=[C:9]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][CH:15]=1)=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium Methoxide2×HCID 43338337(2-Bromo-4-fluoro-phenyl)-(4-ethyl-phenyl)-methanone

Product 1

HCID 58385812(2-Bromo-4-methoxy-phenyl)-(4-ethyl-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium methoxide (10.5 g) is added portionwise to (2-bromo-4-fluoro-phenyl)-(4-ethyl-phenyl)-methanone (43.0 g) dissolved in DMF (200 mL). The solution is stirred overnight, before another portion of sodium methoxide (5.5 g) is added. After another 3 h of stirring, water is added and the resulting mixture is extracted with ethyl acetate. The organic phase is dried (sodium sulphate), the solvent is removed and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 20:1->9:1).

Workup

  1. additionis added
  2. extractionthe resulting mixture is extracted with ethyl acetate
  3. dry with materialThe organic phase is dried (sodium sulphate)
  4. customthe solvent is removed
  5. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 20:1->9:1)

Sources & evidence

ORD record
ord-64982cd771ba48ec9549ceea381e2657
Source dataset
uspto-grants-2011_02
Patent number
US07879806B2

Reaction notes

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