Triethylamine → 2-bromo-N-(4-iodophenyl)acetamide

HRID 1271607Notes

Reaction equation

HRID 1271607 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Br:9][CH2:10][C:11](Br)=[O:12].C(N(CC)CC)C>ClCCl>[Br:9][CH2:10][C:11]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([I:1])=[CH:3][CH:4]=1)=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108934-IodoanilineHCID 61147Bromoacetyl bromide

Product 1

HCID 34153442-bromo-N-(4-iodophenyl)acetamideYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-iodoaniline (14.5 mmol) in anhydrous dichloromethane at 0° C. was added a-bromo-acetylbromide (1.4 mL) and triethylamine (15 mmol). The mixture was warmed to room temperature, stirred for 1 h, the solvent removed, and residue dissolved in 5% hydrochloric acid. The aqueous solution was extracted with ethyl acetate, the organic layer washed with brine, dried (Na2SO4), filtered, and evaporated. The solid residue was purified by recrystallization form ethyl acetate to afford the desired intermediate.

Workup

  1. customthe solvent removed
  2. dissolutionresidue dissolved in 5% hydrochloric acid
  3. extractionThe aqueous solution was extracted with ethyl acetate
  4. washthe organic layer washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid residue was purified by recrystallization
  9. customform ethyl acetate

Sources & evidence

ORD record
ord-2231a9c5512a46028ee46899a2335ba0
Source dataset
uspto-grants-2007_04
Patent number
US07205403B2

Reaction notes

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