2-Bromoethanol → HCID 28977481, compound

HRID 1375657Notes

Reaction equation

HRID 1375657 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Br[CH2:10][CH2:11][OH:12].C([O-])(O)=O.[Na+]>O>[I:1][C:2]1[CH:3]=[C:4]([NH:5][CH2:10][CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 122713-IodoanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 28977481HCID 28977481, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 3-iodoaniline (2.0 g, 9.1 mmol) and 2-bromoethanol (0.32 mL, 4.6 mmol) in a sealed tube was heated at 160° C. for 2 hours. Cooled to room temperature, sat. NaHCO3 and water were added. The resulting mixture was extracted with ethyl acetate, the organic layer was washed with brine, dried, evaporated under reduced pressure. The crude product was purified on a ISCO MPLC to provide the titled compound as a light brown oil (770 mg, 38.6% yield). MS (ESI(+)) m/e 264 (M+H)+.

Workup

  1. temperatureCooled to room temperature
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe crude product was purified on a ISCO MPLC

Sources & evidence

ORD record
ord-40f80bfc9b3448bb9ed033f248c813f9
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

Loading…