反应详情

2-Chloro-5-iodobenzoic acid (10.0 g) was suspended in dichloromethane (160 ml) then oxalyl chloride (4.0 ml) was added followed by N,N-dimethylformamide (40 μl). After 24 h the solvent was evaporated to afford a white solid, which was redissolved in dichloromethane (160 ml). Triethylamine (14.8 ml) was added followed by adamantylmethylamine (6.9 ml) with cooling to maintain a temperature below 30° C. The resulting cloudy mixture was stirred for 1 h, then evaporated to give a pale yellow solid. This was stirred in a mixture of ethyl acetate (400 ml) and 2M hydrochloric acid (300 ml) until the solid dissolved to give 2 clear phases. The (upper) organic phase was separated and washed with 2M aqueous sodium hydroxide solution (300 ml), then dried (Na2SO4) and evaporated to a yellow solid. The solid was suspended in iso-hexane (100 ml), then filtered and washed with more iso-hexane (40 ml). The resulting off-white solid was dried in a vacuum oven at 40° C. (14.0 g).

1. customAfter 24 h the solvent was evaporated
2. customto afford a white solid, which
3. temperaturewith cooling
4. temperatureto maintain a temperature below 30° C
5. customevaporated
6. customto give a pale yellow solid
7. dissolutiondissolved
8. customto give 2 clear phases
9. customThe (upper) organic phase was separated
10. washwashed with 2M aqueous sodium hydroxide solution (300 ml)
11. dry with materialdried (Na2SO4)
12. customevaporated to a yellow solid
13. filtrationfiltered
14. washwashed with more iso-hexane (40 ml)
15. customThe resulting off-white solid was dried in a vacuum oven at 40° C. (14.0 g)