Bromine → 2-(Benzyloxy)-4-bromo-6-methylaniline

HRID 1642649Notes

Reaction equation

HRID 1642649 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[NH2:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]Br>CO.CC(O)=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Br:17])[CH:12]=[C:11]([CH3:15])[C:10]=1[NH2:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 27629472-Benzyloxy-6-methylaniline

Product 1

HCID 588263302-(Benzyloxy)-4-bromo-6-methylaniline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent

Procedure

To a mixture of 2-benzyloxy-6-methylphenylamine (3.4 g, 16 mmol) in MeOH (50 mL) and AcOH (20 mL) is added Br2 (0.82 mL, 16 mmol) in AcOH (10 mL) at 0° C. The mixture is then stirred at ambient temperature for 18 h. The solvent is then removed under reduced pressure. Then K2CO3 solution is added followed by EtOAc. The organic layer is washed with water and brine, dried and concentrated. The residue is then purified by flash chromatography to give the title compound as a red liquid.

Workup

  1. customThe solvent is then removed under reduced pressure
  2. additionThen K2CO3 solution is added
  3. washThe organic layer is washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is then purified by flash chromatography

Sources & evidence

ORD record
ord-a8134201e5714f33b74f32532310e354
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

Loading…