Bromine → 1-Bromo-3-methylnaphthalen-2-ol
Reaction equation
[CH3:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Br:13]Br>C(O)(=O)C>[Br:13][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([CH3:1])[C:3]=1[OH:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Methylnaphthalen-2-ol (4A) (2.09 g, 13.2 mmol) was taken in acetic acid (50 mL) and bromine (2.11 g) was added to it. The mixture was stirred at room temperature for 20 minutes, concentrated and purified by flash chromatography (silica gel, ethyl acetate/hexanes) to give the desired product (2.7 g, 80%). 1H-NMR: 300 MHz, (CDCl3) δ 7.98 (d, 1 H), 7.60 (d, 1 H), 7.58 (s, 1 H), 7.53 (dd, 1 H), 7.38 (dd, 1 H), 6.05 (s, 1 H), 2.48 (s, 3 H).
Workup
- concentrationconcentrated
- custompurified by flash chromatography (silica gel, ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-82a3b2c34c414f7b83e5a6e211463dd3
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102614B2
Reaction notes
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