3-Methoxyphenol → HCID 23289223, compound

Participants

Reaction Steps

3-Methoxyphenol (2.48 g, 20 mmol), 2-bromothiazole (3.28 g, 20 mmol) and Me4N+OH-.5H2O (3.62 g, 20 mmol) were heated in dry DMF (30 mL) under N2 (g) for 16 hours. The mixture was filtered and the filtrate was partitioned between H2O and EtOAc. Organic extracts were pooled, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica (CHCl3) to yield 2.51 g of 2[(3-methoxyphenyl)oxy]thiazole (GC-MS m/z 207 (M+)). A portion (2.42 g, 11.7 mmol) of this material was dissolved in dry CH2Cl2 (40 mL), and BBr3 (2.2 eq.) was added dropwise at about -10° C. under N2 (g). The mixture was allowed to warm to about 20° C., stirred 3 hours, and then poured into ice/H2O and extracted with CH2Cl2. Organic extracts were washed with 5% NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo to yield 3-[(thiazol-2-yl)oxy]phenol as an oil (1.3 g) which was used without further purification (GC-MS m/z 193 (M+)).

Provenance & Evidence