反应 #1702155

反应方程式

3-Bromo-5-methoxybenzonitrile

borane

→

desired product

收率 19.2%

1-(3-Bromo-5-methoxyphenyl)methanamine

收率 19.2%

溶剂

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   温度cooled in an ice bath
2. 2
   workup.ADDITIONAfter the addition
3. 3
   其他quenched slowly with ice water and Na2CO3 (saturated aqueous solution)
4. 4
   其他After removal of THF
5. 5
   萃取the residue was extracted with large amounts of EtOAc three times
6. 6
   洗涤The combined organic layers were washed with water
7. 7
   其他dried
8. 8
   浓缩concentrated
9. 9
   其他to give the crude product, which
10. 10
    其他was purified by silica gel column chromatography

实验过程

3-Bromo-5-methoxybenzonitrile (13.1 g, 61.8 mmol) was dissolved in dry tetrahydrofuran (100 mL) in a flame-dried flask and cooled in an ice bath. A solution of borane in tetrahydrofuran (100 mL, 0.10 mol, 1.0 M) was slowly added over a period of 30 minutes. After the addition was complete, the mixture was heated at 70° C. overnight and quenched slowly with ice water and Na2CO3 (saturated aqueous solution). After removal of THF, the residue was extracted with large amounts of EtOAc three times. The combined organic layers were washed with water, dried, and concentrated to give the crude product, which was purified by silica gel column chromatography to give the desired product as a white powder (2.57 g, 19%). LCMS for C8H10BrNO (M+H)+: m/z=216.9, 218.9.

来源