2-Aminobenzyl alcohol → 2-Amino-5-bromobenzenemethanol

HRID 1816203Notes

Reaction equation

HRID 1816203 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[Br:10]C1C(=O)C(Br)=CC(Br)(Br)C=1>C(Cl)Cl>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 214392-Aminobenzyl alcoholHCID 884332,4,4,6-Tetrabromocyclohexa-2,5-dienone

Product 1

HCID 110308742-Amino-5-bromobenzenemethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-aminobenzyl alcohol (7.12 g, 58 mmol) in methylene chloride (200 mL) at −10° C., 2,4,4,6-tetrabromo-2,5-cyclohexadien-1-one (25 g, 61 mmol) was added in portions. During the addition, the temperature of the reaction mixture was maintained between −10° C. and 0° C. The reaction mixture was warmed up to room temperature and then extracted with 2 N sodium hydroxide solution (2×50 mL). The organic layer was washed with water and dried over MgSO4, filtered and concentrated in vacuo to afford 2-amino-5-bromobenzylalcohol as a yellow solid which was used without further purification.

Workup

  1. additionDuring the addition
  2. temperaturethe temperature of the reaction mixture was maintained between −10° C. and 0° C
  3. extractionextracted with 2 N sodium hydroxide solution (2×50 mL)
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e00c413433924070b07403214a83ec1d
Source dataset
uspto-grants-2005_04
Patent number
US06884782B2

Reaction notes

Loading…