Acetic Acid → 1-Bromo-2-methoxy-6-(4-methoxyphenyl)naphthalene

HRID 1830626Notes

Reaction equation

HRID 1830626 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=2)[CH:4]=1.C(O)(=O)C.[Br:25]Br>O>[Br:25][C:4]1[C:5]2[C:10](=[CH:9][C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 111497342-Methoxy-6-(4-methoxyphenyl)naphthalene

Product 1

HCID 111636961-Bromo-2-methoxy-6-(4-methoxyphenyl)naphthaleneYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-methoxy-6-(4-methoxyphenyl)naphthalene (9.68 g, 36.6 mmol) and glacial acetic acid (150 mL) was slowly added a solution of bromine (5.85 g, 36.6 mmol) in glacial acefic acid (20 mL). The mixture was stirred for 1 hour and the resulting suspension was poured into water (200 mL) and the solid product was collected by filtration. The solid was triturated first with water and then with ethyl acetate to yield 11.25 g (90%) of the title compound as a white solid: mp 172–174° C.; 1H NMR (CDCl3): δ 3.88 (3H, s), 4.05 (3H, s), 7.04 (2H, d, J=8.56 Hz), 7.30 (1H, d, J=9.01 Hz), 7.67 (2H, d, J=8.65 Hz), 7.81 (1H, dd, J=1.61 Hz, J=8.84 Hz), 7.87(1H, J=9.04 Hz), 7.94 (1H, d, J=1.47 Hz), 8.27 (1H, d, J=8.92 Hz); MS (El) m/z 343 (M)+.

Workup

  1. filtrationthe solid product was collected by filtration
  2. customThe solid was triturated first with water

Sources & evidence

ORD record
ord-8c1ee79e64654b80a7d39f82a7312a36
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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