反応 #694207

反応方程式

2-amino-5-(trifluoromethyl)benzonitrile

Intermediate 7

2-amino-5-(trifluoromethyl)benzonitrile

diiodomethane

t-butyl nitrite

→

2-iodo-5-(trifluoromethyl)benzonitrile

溶媒

ether

acetonitrile

反応条件

後処理

1. 1
   温度heated to 60° C. for 30 minutes
2. 2
   温度The reaction mixture was cooled
3. 3
   洗浄washed twice with water, twice with aqueous sodium bisulfite, water
4. 4
   乾燥The solution was dried over anhydrous MgSO4
5. 5
   ろ過filtered through a silica gel plug
6. 6
   濃縮concentrated
7. 7
   その他giving
8. 8
   その他afford a red oil
9. 9
   その他The product was purified by silica gel chromatography
10. 10
    洗浄eluting sequentially with hexanes, 3:1 hexanes/CH2Cl2 and 1:1 hexanes/CH2Cl2

実験手順

To a solution of 2-amino-5-(trifluoromethyl)benzonitrile (Intermediate 7, 15.1 g) and diiodomethane (24 mL) in acetonitrile (150 mL) at 35° C. was added t-butyl nitrite (21 mL) dropwise. The reaction was maintained at approximately 35° C. during the addition. The reaction was aged for 30 min and then heated to 60° C. for 30 minutes. The reaction mixture was cooled, diluted with ether and washed twice with water, twice with aqueous sodium bisulfite, water and then brine. The solution was dried over anhydrous MgSO4, filtered through a silica gel plug and then concentrated giving afford a red oil. The product was purified by silica gel chromatography eluting sequentially with hexanes, 3:1 hexanes/CH2Cl2 and 1:1 hexanes/CH2Cl2 to afford 2-iodo-5-(trifluoromethyl)benzonitrile. 1H NMR (CDCl3, 500 MHz) δ 8.10 (d, J=8.5 Hz, 1H), 7.85 (d, J=1.8 Hz, 1H), 7.52 (dd, J=8.5, 1.8 Hz, 1H).

出典