Boron tribromide → 4-Bromo-2-(2-hydroxyethyl)phenol

HRID 1596709Notes

Reaction equation

HRID 1596709 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11]CC)=[C:6]([CH2:8][CH2:9][OH:10])[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH2:8][CH2:9][OH:10])[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21702621HCID 21702621, compound

Product 1

HCID 217026714-Bromo-2-(2-hydroxyethyl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(5-bromo-2-ethoxyphenyl)-1-ethanol (18.86 g, 81.65 mmol) in 400 mL CH2Cl2 at −78° is added boron tribromide (16.98 mL, 179.6 mmol) dropwise, via syringe. After stirring at −78° for 15 minutes, the solution is warmed to room temperature and stirred for 1 hour. The reaction niuture is then poured into ice water (500 mL), shaken, and separated. The organic phase is wshed with water (1×250 mL) and brine (1×100 mL), dried over MgSO4, and concentrated in vacuo. Chromatography (silica, 2:1 hexane/EtOAc) yields 2-(5-bromo-2-hydroxyphenyl)-1-ethanol.

Workup

  1. stirringstirred for 1 hour
  2. stirringshaken
  3. customseparated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9033293e3dd046d7bfc5fbde961c3629
Source dataset
uspto-grants-2001_09
Patent number
US06291530B1

Reaction notes

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