N-bromobutanimide → 6-Bromo-2,3-dimethoxyphenol

HRID 2171007Notes

Reaction equation

HRID 2171007 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[OH:11].[Br:12]N1C(=O)CCC1=O>O1CCCC1.O>[Br:12][C:5]1[C:4]([OH:11])=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 788282,3-Dimethoxyphenol

Product 1

HCID 139408076-Bromo-2,3-dimethoxyphenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2,3-dimethoxy-phenol (6 g, 38.70 mmol) in tetrahydrofuran (30 mL) at 25° C., was added N-bromosuccinimide (6.89 g, 38.70 mmol) and the resultant reaction mixture was stirred at RT for 1 h. The reaction mixture was diluted with water and extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 6-Bromo-2,3-dimethoxyphenol as a solid.

Workup

  1. customthe resultant reaction mixture
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined ethyl acetate layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f488ba30e6144f49745e5acab537ddb
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

Loading…