Реакция #9333

Уравнение реакции

NH4Cl

4-bromobenzyl alcohol

NaH

4-methoxybenzyl chloride

→

7-2

Выход 98.0%

4-Bromobenzyl (4-methoxybenzyl) ether

Выход 98.0%

Растворители

THF

DMF

Условия реакции

Обработка

1. 1
   workup.WAITAfter 24 h
2. 2
   ЭкстракцияThe resulting mixture was extracted with ethyl acetate (3×60 mL)
3. 3
   Промывкаthe combined ethyl acetate solution was washed with water and brine
4. 4
   СушкаThe solution was then dried (Na2SO4)
5. 5
   Фильтрацияfiltered
6. 6
   Другоеevaporated
7. 7
   ДругоеPurification of the residue by flash chromatography on silica gel (5% ethyl acetate/hexanes)

Методика

A solution of 4-bromobenzyl alcohol (2.011 g, 10.7 mmol) in THF (42 mL) was added to a mixture of NaH (663 mg, 16.6 mmol, 60% in oil) in DMF (13 mL). The mixture was stirred for 1.5 h and 4-methoxybenzyl chloride (MPMCl, 2 mL, 14.8 mmol) was added. After 24 h, 100 mL saturated NH4Cl solution was added. The resulting mixture was extracted with ethyl acetate (3×60 mL) and the combined ethyl acetate solution was washed with water and brine. The solution was then dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (5% ethyl acetate/hexanes) gave 7-2 (2.43 g, 98%).

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