反応 #6917

反応方程式

benzyltrimethyl ammonium dichloroiodate

dichloromethane

2-amino-4-fluoro-benzoic acid

sodium hydrogencarbonate

→

title compound

収率 77.0%

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

収率 77.0%

溶媒

methanol

反応条件

後処理

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

実験手順

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 litre) and a 0.2 N solution of sodium hydroxide (1 litre), added to a 2 litre 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).

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