Bromine → 2-(2-Amino-5-bromo-phenyl)-ethanol

HRID 488654Notes

Reaction equation

HRID 488654 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6].[Br:11]Br>C(O)(=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6]

Participants

4

Reactant 2

HCID 24408BromineHCID 79282o-Aminophenethyl alcohol

Product 1

HCID 219968352-(2-Amino-5-bromo-phenyl)-ethanolYield 100.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

To a solution of 2-aminophenethyl alcohol (10.0 g, 72.9 mmol) in acetic acid (60 mL) at 10° C. was added Br2 (3.8 mL, 72.9 mmol) in acetic acid (5 mL). Additional acetic acid (30 mL) was added and the reaction was stirred for 1 hour. The mixture was filtered and the filter cake washed with diethyl ether. The solid was then partitioned between ethyl acetate and aqueous 3N NaOH. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to provide the titled compound (15.8 g).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake washed with diethyl ether
  3. customThe solid was then partitioned between ethyl acetate and aqueous 3N NaOH
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08e4b1d43a0b4c74983299ec1bcc6281
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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