3-Bromo-N-methoxy-N-methylbenzamide → 1-(3-Bromophenyl)butan-1-one

HRID 30555Notes

Reaction equation

HRID 30555 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5](N(OC)C)=[O:6].[CH2:14]([Mg]Br)[CH2:15][CH3:16]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[CH2:14][CH2:15][CH3:16])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 121628753-Bromo-N-methoxy-N-methylbenzamideHCID 178455851HCID 178455851, compound

Product 1

HCID 184177011-(3-Bromophenyl)butan-1-oneYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cold (0° C.) solution of 3-bromo-N-methoxy-N-methylbenzamide (3 g, 12.3 mmol) in THF was treated with propylmagnesium bromide (6.15 mL, 12.3 mmol), stirred at room temperature for 1 hour, quenched with aqueous NH4Cl, acidified with HCl (2N) and extracted with ethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated under vacuum. Purification of the resultant residue on silica gel (Biotage) using hexanes/EtOAc (20/1) as the eluting solvents gave 1-(3-bromophenyl)butan-1-one as a tan solid (2.1 g, 75% yield).

Workup

  1. customquenched with aqueous NH4Cl
  2. extractionextracted with ethyl ether
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customPurification of the resultant residue on silica gel (Biotage)

Sources & evidence

ORD record
ord-c3c50457fbab42eb9f86fbeda77c61d5
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

Loading…