Triethylamine → 2-(4-bromophenyl)-N,N-dimethylacetamide

HRID 230614Notes

Reaction equation

HRID 230614 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[C:12](N1C=CN=C1)([N:14]1C=CN=[CH:15]1)=O.C(N(CC)CC)C.Cl.CNC>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:14]([CH3:15])[CH3:12])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 46315952-(4-bromophenyl)-N,N-dimethylacetamideYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromophenylacetic acid (960 mg, 4.49 mmol) in dichloromethane (30 ml) was treated in one portion with solid 1,1′-carbonyldiimidazole (730 mg, 4.5 mmol) at 20° C. with stirring under argon. This mixture was allowed to stir at room temperature for 15 minutes. Triethylamine (0.63 ml) was then added followed by dimethylamine hydrochloride (367 mg, 4.5 mmol) and the stirring continued for 1 hour. Most of the solvent was removed under reduced pressure and the residue added to a 20 g isolute silica sep-pak column and eluted from 0-50% ethyl acetate in petroleum ether to give the title compound as a colourless solid (689 mg, 64%).

Workup

  1. stirringto stir at room temperature for 15 minutes
  2. customMost of the solvent was removed under reduced pressure
  3. additionthe residue added to a 20 g isolute silica sep-pak column
  4. washeluted from 0-50% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-029811c8d9194bc08a9aa0df315b6526
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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