2-(3-Fluoro-4-methoxyphenyl)ethanamine → 4-(2-Aminoethyl)-2-fluorophenol

HRID 2386462Notes

Reaction equation

HRID 2386462 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][NH2:12])[CH:5]=[CH:6][C:7]=1[O:8]C>Br>[NH2:12][CH2:11][CH2:10][C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([F:1])[CH:3]=1

Participants

3

Reactant 1

HCID 4263002-(3-Fluoro-4-methoxyphenyl)ethanamine

Product 1

HCID 1932924-(2-Aminoethyl)-2-fluorophenol

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Intermediate 82 was dissolved in 200 mL of 48% aqueous HBr and the mixture heated to reflux for 2 hours. The Solvent was removed by rotary evaporation. The residue was taken up in 100 mL of ethanol and the solvent again removed. This was repeated twice more to remove residual water. LC-MS showed the product was >90% pure had the expected M+H+ of 156.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2 hours
  3. customThe Solvent was removed by rotary evaporation
  4. customthe solvent again removed
  5. customto remove residual water

Sources & evidence

ORD record
ord-4035c7512b6c4308a9a4a02c4ef4de14
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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