3-Methyl-2-nitrophenol → 4-Bromo-3-methyl-2-nitrophenol
Reaction equation
[CH3:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Br:12]Br>C(O)(=O)C>[Br:12][C:7]1[CH:6]=[CH:5][C:4]([OH:8])=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
An ice cold suspension of 3-methyl-2-nitrophenol (6.26 g, 40.9 mmol) in acetic acid (20 mL) was treated with a solution of bromine (1.895 mL, 36.8 mmol) in acetic acid (5.0 mL) over 10 minutes using a syringe pump. The mixture was stirred for one hour at 0° C. The mixture was poured into ice water and then extracted with ethyl acetate. The extracts were washed with 5% sodium bicarbonate (2×50 mL), dried over MgSO4, filtered and then concentrated. The residue was purified on silica gel (hexanes/dichloromethane 0-70% gradient) to afford a bright yellow solid (6.66 g, 70%): 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.32 (s, 1 H), 7.67 (d, J=9.0 Hz, 1 H), 6.93 (d, J=9.0 Hz, 1 H), 2.64 (s, 3 H); LC/MS (m/z) ES+=230 (M−1).
Workup
- extractionextracted with ethyl acetate
- washThe extracts were washed with 5% sodium bicarbonate (2×50 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified on silica gel (hexanes/dichloromethane 0-70% gradient)
Sources & evidence
- ORD record
- ord-50c25b96687c4b65b727d1d78bc92caf
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609653B2
Reaction notes
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