Pyridine → HCID 118005848, compound

HRID 1049623Notes

Reaction equation

HRID 1049623 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([Cl:12])=[CH:7][CH:6]=2.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.N1C=CC=CC=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[Cl:1][C:2]1[CH:3]=[C:4]([O:13][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH3:14])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([Cl:12])=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 1049PyridineHCID 27339582-Methoxyphenylboronic acidHCID 101565766HCID 101565766, compound

Product 1

HCID 118005848HCID 118005848, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3,6-dichloronaphthalen-1-ol (1.0 equiv), 2-methoxyphenylboronic acid (1.5 equiv), Cu(OAc)2 (1.3 equiv), pyridine (5.0 equiv), and 4 Å MS in dry DCM (3.0 mL) was stirred at room temperature for 48 h. The reaction was filtered, concentrated by rotary evaporation, and purified by column chromatography to give 3,6-dichloro-1-(2-methoxyphenoxy)naphthalene (25) (38%). 1H NMR (400 MHz, CDCl3) δ 8.30 (d, J=12.0 Hz, 1H), 7.73 (d, J=4.0 Hz, 1H), 7.44 (dd, J=12.0, 4.0 Hz, 1H), 7.40 (s, 1H), 7.10-7.06 (m, 2H), 7.02 (dd, J=3.4, 1.2 Hz, 1H), 6.96 (d, J=1.2 Hz, 1H), 6.54 (d, J=4.0 Hz, 1H), 3.80 (s, 3H), GC-MS (ES) for C17H12Cl2O2 [M]+ 318.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated by rotary evaporation
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-4c15d76178c947f29aaf191d270059cf
Source dataset
uspto-grants-2016_07
Patent number
US09382245B2

Reaction notes

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