Реакция #216968

Уравнение реакции

1-bromohexane

6-bromo-2-naphthalenol

sodium hydride

→

title compound

Выход 81.0%

2-Bromo-6-(hexyloxy)naphthalene

Выход 81.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred for 60 min
2. 2
   ДругоеThe reaction was quenched with ice water
3. 3
   Фильтрацияthe resultings solids filtered
4. 4
   Промывкаwashed with water
5. 5
   Другоеdried in vacuo at 60° C
6. 6
   ДругоеPurification of the residue by chromatography on silica gel (5×20 cm column, hexanes as elutant)
7. 7
   Другоеgave 5.00 g, 81% yield

Методика

To a stirred solution of 4.46 g (20.0 mmol) of 6-bromo-2-naphthalenol (obtained from Aldrich Chemical Company (#B7,340-6) and used without purification), in 20 mL of DMF at room temperature under argon was added 480 mg (20 mmol) of 95% sodium hydride over the course of 15 min. The resulting light yellow solution was stirred 30 min and 3.5 mL (22 mmol) of 1-bromohexane was added. The reaction was heated to 50° C. and stirred for 60 min. The reaction was quenched with ice water, the resultings solids filtered, washed with water and dried in vacuo at 60° C. Purification of the residue by chromatography on silica gel (5×20 cm column, hexanes as elutant) gave 5.00 g, 81% yield, of title compound as a colorless oil.

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