Potassium Carbonate → 1-Bromo-2-methoxy-4-propoxybenzene

HRID 612613Notes

Reaction equation

HRID 612613 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH2:17](I)[CH2:18][CH3:19]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH2:18][CH3:19])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 3479554-Bromo-3-methoxyphenol

Product 1

HCID 195949351-Bromo-2-methoxy-4-propoxybenzeneYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Prepare a solution of 4-bromo-3-methoxyphenol (6.5 g, 32 mmole), and potassium carbonate (15 g) in acetone (250 mL) under argon. Add n-propyl iodide (9.0 g, 5.2 mL, 53 mmole) and heat to reflux overnight. Cool to room temperature and filter. Rotovap to condense and evaporate the solvents. Check by thin layer chromatagraphy (25% ethyl aceate/75% hexane). Wash three times with 100 mL 3% potassium hydroxide. Dry the organic layer with magnesium sulfate. Filter and rotovap. Purify by chromatography and place under high vacuum to obtain the title compound (6.9 g, 88%). Rf=0.60 (EtOAc/hexane; 25:75).

Workup

  1. temperatureto reflux overnight
  2. filtrationfilter
  3. customRotovap to condense
  4. customevaporate the solvents
  5. washWash three times with 100 mL 3% potassium hydroxide
  6. dry with materialDry the organic layer with magnesium sulfate
  7. filtrationFilter
  8. customPurify by chromatography and place under high vacuum

Sources & evidence

ORD record
ord-c7076e5a361e4647a2e6332bb7696652
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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