Boron tribromide → 4-Bromocatechol

HRID 1978613Notes

Reaction equation

HRID 1978613 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([Br:15])[CH:10]=[CH:11][C:12]=1[O:13]C>ClCCl>[Br:15][C:9]1[CH:8]=[C:7]([OH:6])[C:12](=[CH:11][CH:10]=1)[OH:13]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 76114Benzene, 4-bromo-1,2-dimethoxy-

Product 1

HCID 284874-BromocatecholYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of boron tribromide (25 g) in dichloromethane (100 ml) was added dropwise at 0° C. a solution of 3,4-dimethoxybromobenzene (10.0 g) in dichloromethane (20 ml), and the mixture was stirred at room temperature for 15 hours and then added to ice/water to stop the reaction. The mixture was extracted with diethylether, and the organic layer was washed with saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give colorless crystals of 4-bromocathechol (8.43 g).

Workup

  1. customthe reaction
  2. extractionThe mixture was extracted with diethylether
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c3e29adc4684515bdc8be4e1e954f32
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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