Triethylamine → 2-(3-Bromoanilino)ethan-1-ol

HRID 269744Notes

Reaction equation

HRID 269744 reaction equation
[Br: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(N(CC)CC)C>C1(C)C=CC=CC=1>[Br: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 8471TriethylamineHCID 108982-BromoethanolHCID 115623-Bromoaniline

Product 1

HCID 221628942-(3-Bromoanilino)ethan-1-olYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-bromo-aniline (0.037 mol), 2-bromo-ethanol (0.074 mol) and triethylamine (0.0555 mol) in toluene (35 ml) was stirred under reflux for 12 hours. The reaction was cooled down to room temperature and the precipitate was filtered off. The solvent of the filtrate was evaporated until dryness. The residue (22 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 98/2/0.1; 20-45 μm). The pure fractions were collected and the solvent was evaporated, yielding 4.8 g of 2-(3-bromo-phenylamino)-ethanol (60%).

Workup

  1. temperatureunder reflux for 12 hours
  2. filtrationthe precipitate was filtered off
  3. customThe solvent of the filtrate was evaporated until dryness
  4. customThe residue (22 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 98/2/0.1; 20-45 μm)
  5. customThe pure fractions were collected
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-26c7b3623e2d4c98bb47200622cd98b8
Source dataset
uspto-grants-2008_11
Patent number
US07449463B2

Reaction notes

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