Reaktion #733206

Reaktionsgleichung

methyl 6-bromo-2-naphthoate

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Na2CO3

→

methyl 6-(4-hydroxyphenyl)-2-naphthoate

Lösungsmittel

dimethoxyethane

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthen filtered through a plug of Celite and silica gel
2. 2
   WaschenThe filtrate was washed with H2O
3. 3
   Trocknenbrine, dried over Na2SO4
4. 4
   Einengenconcentrated
5. 5
   Sonstigepurified by silica gel chromatography (40 g of silica gel eluting with 0-50% EtOAc in hexanes over 45 minutes)

Vorschrift

To a solution of methyl 6-bromo-2-naphthoate (150 mg, 0.57 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (150 mg, 0.68 mmol), and 2.0 M Na2CO3 (1.10 mL, aq) in dimethoxyethane (5 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (14 mg, 0.02 mmol) and the mixture stirred at 70° C. for 20 min. The mixture was diluted with 25 mL of EtOAc then filtered through a plug of Celite and silica gel. The filtrate was washed with H2O, then brine, dried over Na2SO4, then concentrated and purified by silica gel chromatography (40 g of silica gel eluting with 0-50% EtOAc in hexanes over 45 minutes) to give methyl 6-(4-hydroxyphenyl)-2-naphthoate as a beige solid (55 mg, 35%.) 1H NMR (DMSO-d6): δ 9.67 (s, 1H), 8.60 (s, 1 H), 8.17-8.13 (m, 2 H), 8.02 (d, J=9 Hz, 1 H), 7.95 (d, J=9 Hz, 1 H), 7.87 (d, J=9 Hz, 1H), 7.67 (d, J=8 Hz, 2H), 6.89 (d, J=8 Hz, 2H), 3.89 (s, 3H). ESI-LCMS m/z 279 (M+H)+.

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