反应 #79375

反应方程式

benzyltrimethyl ammonium dichloroiodate

dichloromethane

2-amino-4-fluoro-benzoic acid

sodium hydrogencarbonate

→

title compound

收率 77.0%

2-Amino-4-fluoro-5-iodo-benzoic acid

收率 77.0%

溶剂

methanol

反应条件

后处理

1. 1
   过滤The mixture was filtered
2. 2
   其他to remove the insolubles
3. 3
   洗涤The remaining solid residue was washed with 200 ml of dichloromethane
4. 4
   浓缩The filtrate was concentrated
5. 5
   workup.DISSOLUTIONredissolved in a one to one mixture of ethyl acetate (1 liter)
6. 6
   workup.ADDITIONa 0.2 N solution of sodium hydroxide (1 liter), added to a 2 liter separatory funnel
7. 7
   萃取extracted
8. 8
   洗涤The organic layer was washed with an additional 200 ml of water
9. 9
   过滤The resulting precipitate was collected by suction filtration
10. 10
    洗涤washed with water
11. 11
    其他dried under vacuum at 60° C.

实验过程

To a vigorously stirred solution of dichloromethane (700 ml), methanol (320 ml), and 2-amino-4-fluoro-benzoic acid (33.35 grams, 215 mmoles) was added solid sodium hydrogencarbonate (110 grams, 1.31 moles) followed by portion addition of benzyltrimethyl ammonium dichloroiodate (82.5 grams, 237 mmoles). The mixture was allowed to stir for 48 hours. The mixture was filtered to remove the insolubles. The remaining solid residue was washed with 200 ml of dichloromethane. The filtrate was concentrated and redissolved in a one to one mixture of ethyl acetate (1 liter) and a 0.2 N solution of sodium hydroxide (1 liter), added to a 2 liter separatory funnel and extracted. The organic layer was washed with an additional 200 ml of water. The aqueous layers were combined and acidified with 2N hydrochloric acid. The resulting precipitate was collected by suction filtration, washed with water and dried under vacuum at 60° C. to yield 46.5 grams (77%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ: 8.04(d, 1H), 7.1(s, broad, 2H), 6.63(d, 1H). ESI-MS m/z 280 (M−1).

来源