Hydrochloric Acid → 3-Bromo-2-methoxybenzaldehyde

HRID 1037276Notes

Reaction equation

HRID 1037276 reaction equation
[Br:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:11](=O)([O-])[O-].[K+].[K+].IC.Cl>CN(C=O)C>[Br:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 109105553-Bromo-2-hydroxybenzaldehyde

Product 1

HCID 110638083-Bromo-2-methoxybenzaldehydeYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-2-hydroxy-benzaldehyde (2.72 g, 13.53 mmol) in DMF (70 mL) were added potassium carbonate (5.61 g, 40.59 mmol) and iodomethane (1.01 mL, 16.24 mmol). The reaction mixture was stirred at RT. After 18 h, the mixture was acidified with cooling using 1 M HCl (aq), extracted with EtOAc. The organic extract was dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound as an oil (2.73 g, 94%). 1H NMR (300 MHz, CDCl3): δ 10.36 (s, 1H), 7.85-7.79 (m, 2H), 7.15 (dt, J=7.7 and 0.7 Hz, 1H), 4.00 (s, 3H).

Workup

  1. temperaturewith cooling
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93087c2dc3e34bf09c9408daf7a60448
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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