Реакция #339412

Уравнение реакции

2-bromo-4-fluoro-phenol

p-toluenesulphonic acid

dimethoxymethane

→

title compound

2-bromo-4-fluoro-1-(methoxymethoxy)benzene

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   Температураthe resulting mixture was heated
2. 2
   Температураunder reflux for 16 h under a soxhlett apparatus
3. 3
   workup.ADDITIONcharged with freshly dried molecular 4 Å
4. 4
   Промывкаwashed with 2M sodium hydroxide (100 mL)
5. 5
   Сушкаthen dried (Na2SO4)
6. 6
   Фильтрацияfiltered
7. 7
   Другоеthe solvent was evaporated under vacuum

Методика

To a solution of 2-bromo-4-fluoro-phenol (1 g, 5.23 mmol) in CH2Cl2 (120 mL) was added p-toluenesulphonic acid (0.07 g, mmol), dimethoxymethane (2.31 mL, 26.15 mmol) and the resulting mixture was heated under reflux for 16 h under a soxhlett apparatus charged with freshly dried molecular 4 Å sieves. The reaction was allowed to warm to room temperature and washed with 2M sodium hydroxide (100 mL) then dried (Na2SO4), filtered and the solvent was evaporated under vacuum to give title compound as an oil: 0.567 g, 46%. 1H-NMR (CDCl3, 300 MHz) δ7.31 (dd, 1H, J=2.9, 7.9 Hz, ArH), 7.13 (dd, 1H, J=4.9, 9.1 Hz, ArH), 6.98 (m, 1H, ArH), 5.21 (s, 2H, —OCH2O—), 3.54 (s, 3H, —OCH3)

Источник