Water → 1,2-Benzenediol, 3-bromo-

HRID 1251363Notes

Reaction equation

HRID 1251363 reaction equation
C[O:2][C:3]1[C:8]([O:9]C)=[CH:7][CH:6]=[CH:5][C:4]=1[Br:11].[Al+3].[Cl-].[Cl-].[Cl-].O>C1(C)C=CC=CC=1>[OH:2][C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:4]=1[Br:11]

Participants

5

Reactant 3

HCID 962WaterHCID 2240131-bromo-2,3-dimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 266591,2-Benzenediol, 3-bromo-Yield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2,3-dimethoxy-bromobenzene (8.2 g, 0.45 moles) in 50 mL of toluene was added AlCl3 (22.1 g, 0.178 moles). The reaction mixture was refluxed for 3 hours, cooled, poured into 800 mL of water, and extracted with 800 mL of ether. The ether extracts were dried over magnesium sulfate, filter and the solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluted with methylene chloride and the fraction were combined and evaporated under reduced pressure to yield 2,3-dihydroxy-bromobenzene (6.1 g, 73% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. temperaturecooled
  3. extractionextracted with 800 mL of ether
  4. dry with materialThe ether extracts were dried over magnesium sulfate
  5. filtrationfilter
  6. customthe solvent removed under reduced pressure
  7. customThe residue was chromatographed on silica gel
  8. washeluted with methylene chloride
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-328a1071789643359c102e17fabdadca
Source dataset
uspto-grants-2002_01
Patent number
US06342504B1

Reaction notes

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