Triethylamine → 2-bromo-N-(3-iodophenyl)acetamide

HRID 2273347Notes

Reaction equation

HRID 2273347 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Br:9][CH2:10][C:11](Br)=[O:12].CCN(CC)CC>C(Cl)Cl>[Br:9][CH2:10][C:11]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([I:1])[CH:3]=1)=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122713-IodoanilineHCID 61147Bromoacetyl bromide

Product 1

HCID 448834702-bromo-N-(3-iodophenyl)acetamideYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-iodoaniline (2.19 g, 10.0 mmol) and 2-bromoacetyl bromide (0.87 mL, 3.40 g, 10.0 mmol) in DCM (100 mL) was added Et3N (1.39 mL) at 0° C. The reaction mixtures were stirred at room temperature for overnight. The reaction mixtures were diluted with DCM (100 mL), washed with water, and dried over Na2SO4. Solvent was evaporated under reduce pressure to afford a residue, which was purified by biotage eluting with 10% EtOC in hexanes to 100% EtOAc to afford 2-bromo-N-(3-iodophenyl)acetamide (2.824 g, 83%). MS (ESI), 340, 342 (M+H)+.

Workup

  1. customThe reaction mixtures
  2. customThe reaction mixtures
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customSolvent was evaporated
  6. customto afford a residue, which
  7. customwas purified by biotage
  8. washeluting with 10% EtOC in hexanes to 100% EtOAc

Sources & evidence

ORD record
ord-4bbd2a986e0e4f2d96fa2b7244dd00d3
Source dataset
uspto-grants-2015_09
Patent number
US09120837B2

Reaction notes

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