Boron tribromide → 4-(4-Methylphenoxy)phenol
Reaktionsgleichung
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[C:13]1([CH3:16])[CH:12]=[CH:11][C:10]([O:9][C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)=[CH:15][CH:14]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
1-methoxy-4-(4-methylphenoxy)benzene (23.50 g, 0.110 mol) was taken into anhydrous dichloromethane (100 mL). The mixture was cooled to −78° C. Boron tribromide (82.43 g, 0.329 mol) in anhydrous dichloromethane (100 mL) was added to the reaction dropwise over 10 min. The reaction was kept at −78° C. for 2 h. and was then allowed to warm to room temperature overnight. The reaction was then cooled to 0° C. and quenched with methanol. The mixture was concentrated to dryness and the residue taken into dichloromethane. The pH was adjusted to ˜8 with sodium bicarbonate (aq). The mixture was partitioned and the aqueous layer was washed with dicholoromethane (3×). The combined organic layers were washed with water (2×), brine (1×) and concentrated to dryness to obtain the title product (18.29 g, 0.091 mol, 83% yield); LCMS, m/z 200. found 199 (M−H). 1H NMR (400 MHz, DMSO-d6) δ 2.25 (s, 3H), 6.74-6.85 (m, 6H), 7.10-7.13 (m, 2H), 9.28 (s, 1H).