2-Fluoro-6-methoxynaphthalene → 6-Fluoronaphthalen-2-ol
반응식
[F:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12]C)[CH:8]=2)[CH:3]=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2참가 물질
3
반응 조건
- 온도
- 0 °C
실험 절차
A flask was charged with 2-fluoro-6-methoxynapthalene (3.80 g, 21.6 mmol) and dichloromethane (86 mL) and cooled to 0° C. in an icebath under a flow of nitrogen. A solution of borontribromide (26 mL of a 1M solution in dichloromethane, 25.9 mmol) was added via cannula. The reaction solution was stirred 15 minutes at 0° C., the cooling bath was removed and the reaction was stirred for 1.5 h at ambient temperature. The reaction was quenched by slowly adding excess 10% aqueous hydrochloric acid. The two-phased reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed (2x, brine), dried (Na2SO4), filtered and concentrated in vacuo to afford a brown gummy solid. Purification by flash chromatography (silica gel; 20% ethyl acetate/hexane) afforded the desired product (3.63 g, 91% yield). Recrystallization from cold ether/hexanes provided the title compound as a colorless powdery solid. mp 118°-120° C.; 1HNMR (300 MHz, DMSO-d6) δ 7.11-7.18 (m; 2H), 7.30 (td; J=9,9,3 Hz; 1H), 7.55 (dd; J=10.5,3 Hz; 1H), 7.73-7.79 (m; 2H), 9.73 (s; 1H).