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

HRID 895177

Reaction equation

HRID 895177 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.[Br:21]Br.O>C(O)(=O)C>[Br:21][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 962WaterHCID 24408BromineHCID 111497342-Methoxy-6-(4-methoxyphenyl)naphthalene

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

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 acetic 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, d, J=9.04 Hz), 7.94 (1H, d, J=1.47 Hz), 8.27 (1H, d, J=8.92 Hz); MS (EI) 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-32399ce89bf94e0192952c589451be8c
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Linked notes

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