C([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]2[C:8](=[C:9]([Br:22])[CH:10]=[CH:11][C:12]=2[O:18][CH:19]([CH3:21])[CH3:20])[CH:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.Cl>C1COCC1>[Br:22][C:9]1[C:8]2[C:13](=[C:14]([O:16][CH3:17])[CH:15]=[C:6]([CH2:4][OH:3])[CH:7]=2)[C:12]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:11][CH:10]=1
A solution of 4.80 g (13.1 mmol) ethyl-8-bromo-5-isopropoxy-4-methoxy-2-naphthoate in 100 mL dry THF was cooled to 0° C. under Ar. A suspension of 498 mg (13.1 mmol) LiAlH4 in 60 mL dry THF was cooled to 0° C. and added to the ester over a period of 45 min. After stirring for 30 min at 0° C., 10 mL water and 10 mL 2N HCl were added carefully. The THF was concentrated in vacuo and the residue was extracted with dichloromethane, dried (MgSO4) and concentrated in vacuo. Column chromatography (dichloromethane/acetone, 95:5) afforded 4.00 g (95%) 1-bromo-7-hydroxymethyl-4-isopropoxy-5-methoxy-naphthalene as colorless needles (m.p. 120°-121° C.).
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