4-Methoxyphenol → 2-Bromo-4-methoxyphenol
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
Product 1
Reagents, catalysts & solvents 1
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, 1H), 6.96 (d, 1H), 6.72-6.62 (m, 2H), 3.71 (s, 3H).
Workup
- customwas quenched with water
- extractionextracted with ethyl acetate (3×200 mL)
- washThe combined organic extracts were washed with brine
- dry with materialdried (Na2SO4)
- customRemoval of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-0c1a1ef94a6c4000a7468b73f127b7f0
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05958968
Reaction notes
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