Formaldehyde → 3-Bromo-2-hydroxybenzaldehyde

HRID 2233328Notes

Reaction equation

HRID 2233328 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Cl-].[Mg+2].[Cl-].[CH2:12]=[O:13].CCN(CC)CC>C(#N)C.Cl>[Br:1][C:2]1[C:3]([OH:8])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH:12]=[O:13]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 72442-BromophenolHCID 8471TriethylamineHCID 5360315Magnesium Chloride

Product 1

HCID 109105553-Bromo-2-hydroxybenzaldehydeYield 14,311.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-bromophenol (3.17 g, 18.3 mmol) in acetonitrile (85 mL) was added magnesium chloride (2.62 g, 27.5 mmol), paraformaldehyde (3.7 g, 0.13 mmol) and Et3N (6.4 ml, 46 mmol). The reaction was heated at reflux for 3 h, allowed to cool, diluted with 1 N HCl (100 mL, and extracted with ethyl acetate. The organic layer was washed with aqueous sodium chloride, dried (MgSO4), and concentrated to afford the title compound (3.74 g, 100%): MS (ES) m/e 202.1 (M+H)+. This was used without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3 h
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with aqueous sodium chloride
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-79a40ca60e954ae3943aff30fb7daefd
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

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