Bromine → 1-Bromo-3-methylnaphthalen-2-ol

HRID 514004Notes

Reaction equation

HRID 514004 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

HCID 24408BromineHCID 870503-Methyl-2-naphthol

Product 1

HCID 671260591-Bromo-3-methylnaphthalen-2-olYield 86.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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

  1. concentrationconcentrated
  2. 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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