Boron tribromide → 5-bromobenzene-1,3-diol

HRID 422149Notes

Reaction equation

HRID 422149 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[C:4]([O:10]C)[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([OH:8])[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 6391871-Bromo-3,5-dimethoxybenzene

Product 1

HCID 5573835-bromobenzene-1,3-diolYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (35) (15.0 g, 69.0 mmol) in CH2Cl2 (40 mL), cooled to 0° C., a 1 M BBr3 solution in CH2Cl2 (140 mL, 140 mmol) was added dropwise. The ice bath was removed and the reaction was stirred at room temperature for 18 h. The reaction was quenched with MeOH and concentrated. The residue was dissolved in EtOAc (500 mL) and washed with water (300 mL). The organic layer was separated, dried (Na2SO4) and concentrated to give 5-bromobenzene-1,3-diol (45) (13.03 g, >99%) as an orange oil.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was quenched with MeOH
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in EtOAc (500 mL)
  5. washwashed with water (300 mL)
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1863cebc302846369949fe1fb17e7d90
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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