2-Bromonaphthalene → 2-(4-Methoxyphenyl)naphthalene

HRID 1830619Notes

Reaction equation

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

Participants

Reactant 2

HCID 113722-Bromonaphthalene

HCID 178491912HCID 178491912, compound

Product 1

HCID 111490142-(4-Methoxyphenyl)naphthalene

Procedure

The title compound was prepared by reacting 2-bromonaphthalene (3.04 g, 14.7 mmol) with 4-methoxyphenylmagnesium bromide according to method used to prepared intermediated 10 to yield 2.89 g (89%) of a white solid: mp 114° C.; 1H NMR (CDCl3): δ 3.86 (3H, s), 7.01 (2H, d, J=9.06 Hz), 7.43–7.50 (2H, m), 7.65 (2H, d, J=8.73 Hz), 7.71 (1H, dd, J=1.84 Hz, J=8.56 Hz), 7.83–7.89 (3H, m), 7.98 (1H, d, J=0.67 Hz); MS (El) m/z 234 (M)+.

Workup

customto prepared intermediated 10

Sources & evidence

ORD record: ord-74038667cce54aa3bcd7243ad62df1be
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

Loading…