Water → 2-Bromo-5-methoxybenzaldehyde

HRID 501708Notes

Reaction equation

HRID 501708 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].CI.[C:13](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3871792-Bromo-5-hydroxybenzaldehyde

Product 1

HCID 3444802-Bromo-5-methoxybenzaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step AH (1): To a solution of 2-bromo-5-hydroxybenzaldehyde (1000.0 mg, 4.975 mmol) in DMF (20 mL) were added methyl iodide (0.31 mL, 5.000 mmol) and potassium carbonate (1036.6 mg, 7.500 mmol). The reaction mixture was stirred at rt for 2.5 days. Water was added and the reaction mixture was extracted with hexanes-ether (1:1) solvent system. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuum to yield 2-bromo-5-methoxybenzaldehyde (1069.8 mg, 100%) as colorless oil. LC-MS (M+H)+=215.11. 1H NMR (500 MHz, DMSO-d6) δ 10.18 (s, 1H). 7.70 (d, J=10 Hz, 1H) 7.35 (d, J=3 Hz, 1H) 7.23 (dt, J1=7.0 Hz, J2=2.0 Hz, 1H) 3.83 (s, 3H).

Workup

  1. extractionthe reaction mixture was extracted with hexanes-ether (1:1) solvent system
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-27c125c1195f4a78bd11ba96d3afe800
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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