Chlorosuccinimide → 1-Chloro-2-methoxy-6-(4-methoxyphenyl)naphthalene

HRID 1830627Notes

Reaction equation

HRID 1830627 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.C1C(=O)N([Cl:28])C(=O)C1>C(#N)C>[Cl:28][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

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 111497342-Methoxy-6-(4-methoxyphenyl)naphthalene

Product 1

HCID 111623351-Chloro-2-methoxy-6-(4-methoxyphenyl)naphthaleneYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-methoxy-6-(4-methoxyphenyl)naphthalene (0.51 g, 1.93 mmol) and NCS (0.28 g, 2.13 mmol) in acetonitrile (20 mL) was heated to reflux for 3 hr. The resulting solution was cooled to room temperature and the resulting solid was collected by filtration and rinsed with acetonitrile to yield 0.41 g (72%) of the title compound as a white solid: mp 158–164° C.; 1H NMR (CDCl3): δ 3.87 (3H, s), 4.05 (3H, s), 7.03 (2H, d, J=8.62 Hz), 7.32 (1H, d, J=9.02 Hz); 7.65 (2H, d, J=8.55 Hz), 7.82 (2H, d, J=9.01 Hz), 7.95 (1H, d, J=1.36 Hz), 8.27 (1H, d, J=8.81 Hz); MS (El) m/z 298 (M)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hr
  3. filtrationthe resulting solid was collected by filtration
  4. washrinsed with acetonitrile

Sources & evidence

ORD record
ord-f08738859aae425ca53dd2b360c31f90
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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