Dimethylamine → 5-Bromo-2-iodo-N,N-dimethylbenzeneacetamide

HRID 1270781Notes

Reaction equation

HRID 1270781 reaction equation
[CH3:1][NH:2][CH3:3].[Br:4][C:5]1[CH:6]=[CH:7][C:8]([I:15])=[C:9]([CH2:11][C:12](Cl)=[O:13])[CH:10]=1.CCOC(C)=O>CCOCC>[CH3:1][N:2]([CH3:3])[C:12](=[O:13])[CH2:11][C:9]1[CH:10]=[C:5]([Br:4])[CH:6]=[CH:7][C:8]=1[I:15]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8857Ethyl AcetateHCID 18451527HCID 18451527, compound

Product 1

HCID 184515625-Bromo-2-iodo-N,N-dimethylbenzeneacetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dimethylamine (200 mL of 2 M in THF) is added dropwise to a solution of the above 5-bromo-2-iodophenylacetyl chloride in Et2O (500 mL), cooled in an ice bath. After the addition is complete, EtOAc (350 mL) is added and the solution washed with water (350 mL), brine (250 mL) and dried (MgSO4). Evaporation by rotary evaporator and trituration with 1:1 Et2O/hexanes gives N,N-dimethyl-5-bromo-2-iodophenylacetamide (m.p. 127–129° C.).

Workup

  1. temperaturecooled in an ice bath
  2. additionAfter the addition
  3. washthe solution washed with water (350 mL), brine (250 mL)
  4. dry with materialdried (MgSO4)
  5. customEvaporation
  6. customby rotary evaporator and trituration with 1:1 Et2O/hexanes

Sources & evidence

ORD record
ord-037522addc6b4497932f73570b6004f5
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

Loading…