4-Methoxyphenol → 2-Bromo-4-methoxyphenol

HRID 1870500Notes

Reaction equation

HRID 1870500 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[Br:10]Br>CN(C=O)C>[Br:10][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[OH:9]

Participants

4

Reactant 2

HCID 90154-MethoxyphenolHCID 24408Bromine

Product 1

HCID 2973822-Bromo-4-methoxyphenolYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methoxyphenol (13.00 g, 104.84 mmol) in DMF (50 mL) was added bromine (5.40 mL, 104.84 mmol) at 0° C. The reaction was allowed to warm to room temperature. After stirring for 2 h the reaction was quenched with water and extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent under reduced pressure gave 21.28 g of the crude title compound as a dark oil: 1H NMR (250 MHz, CDCl3) d 7.49 (b, 1 H), 6.96 (d, 1 H), 6.72-6.62 (m, 2 H), 3.71 (s, 3 H).

Workup

  1. customwas quenched with water
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-36799bc5295a433d8df9ce85445620cf
Source dataset
uspto-grants-2000_08
Patent number
US06096897

Reaction notes

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