2-Bromophenol → 3-Bromo-2-hydroxybenzaldehyde

HRID 2173289Notes

Reaction equation

HRID 2173289 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Mg+2].[Cl-].[Cl-].C[CH2:13][O:14]C(C)=O>C1COCC1>[Br:1][C:2]1[C:3]([OH:8])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH:13]=[O:14]

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 8857Ethyl AcetateHCID 5360315Magnesium Chloride

Product 1

HCID 109105553-Bromo-2-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromophenol (48.5 g, 0.28 mol) in 500 mL of THF was added TEA (200 mL) and then MgCl2 (100 g, 1.05 mol) was added portionwise over 90 minutes. The reaction mixture was allowed to stir overnight under a nitrogen atmosphere. The reaction mixture was neutralized with phosphoric, and then exacted with EtOAc (1000 mL). The organic layers were washed with brine (200 mL), dried over Na2SO4. The solvent was concentrated in vacuo. The residue was purified with silica gel chromatography (petrol ether/EtOAc=5:1) to give product 3-bromo-2-hydroxybenzaldehyde.

Workup

  1. washThe organic layers were washed with brine (200 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationThe solvent was concentrated in vacuo
  4. customThe residue was purified with silica gel chromatography (petrol ether/EtOAc=5:1)

Sources & evidence

ORD record
ord-f72205b51af94a4aa007abe36550d17a
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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