Реакция #48718

Уравнение реакции

n-butyl lithium

1-bromo-3-fluoro-5-benzyloxy-benzene

N,N-dimethylformamide

→

desired compound

Выход 32.0%

3-benzyloxy-5-fluoro-benzaldehyde

Выход 32.0%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Температураcooled in a dry ice/acetone bath
2. 2
   Температураmaintaining the internal temperature <−70°
3. 3
   workup.STIRRINGStir 30 minutes
4. 4
   Другоеremove cold bath
5. 5
   workup.WAITAfter 1 hour
6. 6
   Другоеquench with saturated aqueous ammonium chloride
7. 7
   СушкаDry (sodium sulfate)
8. 8
   Фильтрацияfilter
9. 9
   Концентрированиеconcentrate to an oil
10. 10
    ДругоеPurify on 120 g silica gel eluting with 100:0 to 90:10 hexanes

Методика

Add n-butyl lithium (35 mL, 1.6M, 55.96 mmol) over 15 minutes to 1-bromo-3-fluoro-5-benzyloxy-benzene (14.30 g, 50.87 mmol) in tetrahydrofuran (300 mL) cooled in a dry ice/acetone bath, maintaining the internal temperature <−70°. Stir 30 minutes and add N,N-dimethylformamide (7.44 g, 101.74 mmol). Stir 30 minutes and remove cold bath. After 1 hour, quench with saturated aqueous ammonium chloride. Wash organic layer with water and saturated aqueous sodium chloride. Dry (sodium sulfate), filter and concentrate to an oil. Purify on 120 g silica gel eluting with 100:0 to 90:10 hexanes:ethyl acetate to give 3.75 g (32%) of the desired compound as an oil.

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