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

HRID 660829Notes

Reaction equation

HRID 660829 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.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 AcidSolventHCID 10129899Acetic acid methanolSolvent

Procedure

A solution of 2-benzyloxy-6-methyl-phenylamine (3.4 g, 16 mmol) in MeOH/AcOH (50 mL/20 mL) is cooled to 0° C. then a solution of Br2 (0.82 mL, 16 mmol) in AcOH (10 mL) is added dropwise. After the addition, the solution is stirred at RT overnight. The solvent is removed under reduced pressure and the residue adjusted to pH>8 with aqueous K2CO3 solution. The suspension is extracted with EtOAc and the combined organic layers are washed with water, brine, then dried over MgSO4 and filtered. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (hexanes/EtOAc=10:1 to 5:1) to give the title compound as a red solid.

Workup

  1. additionAfter the addition
  2. customThe solvent is removed under reduced pressure
  3. extractionThe suspension is extracted with EtOAc
  4. washthe combined organic layers are washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent is removed under reduced pressure
  8. customthe residue is purified by flash chromatography (hexanes/EtOAc=10:1 to 5:1)

Sources & evidence

ORD record
ord-cc6cbc3c5fc146f08081f28300118297
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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