反応 #499296

反応方程式

water

2-bromophenol

sodium hydride

bromomethyl methyl ether

→

title compound

収率 53.1%

2-methoxymethoxybromobenzene

収率 53.1%

溶媒

DMF

反応条件

後処理

1. 1
   workup.STIRRINGAfter stirring for 16 h at room temperature
2. 2
   抽出extracted with hexane
3. 3
   洗浄The organic layer was washed with brine
4. 4
   乾燥dried (MgSO4)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他The residue was purified by column chromatography (silica gel, hexane)

実験手順

To a stirring suspension of sodium hydride (1.2 g, 52.1 mmol, 60% dispersion in mineral oil) in DMF (75 mL) at 0° C. was added 2-bromophenol (6.0 g, 34.7 mmol) dropwise. After stirring for 20 min, bromomethyl methyl ether (4.3 g, 34.7 mmol) was added. After stirring for 16 h at room temperature, the mixture was poured into water (250 mL) and extracted with hexane. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography (silica gel, hexane) to yield the title compound as a colorless oil (4.0 g, 53%). 1HNMR (400 MHz, CDCl3) δ 7.55 (d, 1H), 7.28 (t, 1H), 7.16 (d, 1H), 6.91 (t, 1H), 5.25 (s, 2H), 3.54 (s, 3H).

出典