反应 #2286298

反应方程式

sodium acetate

[3,5-dibromo-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-proprionic acid

3-[3,5-Dibromo-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-propionic acid

→

[3,5-dibromo-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-proprionic acid

收率 72.0%

3-[3,5-Dibromo-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-propionic acid

收率 72.0%

溶剂

acetic acid

反应条件

后处理

1. 1
   温度The reaction mixture was cooled to room temperature
2. 2
   浓缩concentrated
3. 3
   workup.ADDITIONThe resulting residue was diluted with water (200 mL)
4. 4
   workup.ADDITIONwas made basic to pH=9 by the addition of a 1N aqueous sodium hydroxide solution
5. 5
   萃取This solution was extracted with ethyl acetate (1×100 mL)
6. 6
   workup.ADDITIONThe water layer was acidified to pH=3 by the addition of a 1N aqueous hydrochloric acid solution
7. 7
   萃取The water layer was extracted with ethyl acetate (3×100 mL)
8. 8
   干燥dried with sodium sulfate
9. 9
   过滤filtered
10. 10
    浓缩concentrated under vacuum
11. 11
    workup.ADDITIONHeptane (20 mL) was added to this mixture
12. 12
    浓缩The solvents were then concentrated under vacuum to a volume of approximately 20 mL
13. 13
    过滤The solids were filtered
14. 14
    洗涤washed with a 1:1 ethyl acetate
15. 15
    其他The solid was dried under high vacuum

实验过程

A mixture of glacial acetic acid (16.7 mL), sodium acetate (480 mg, 5.85 mmol) and [3,5-dibromo-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-proprionic acid (22) (800 mg, 1.67 mmol) was heated to 120° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated. The resulting residue was diluted with water (200 mL) and was made basic to pH=9 by the addition of a 1N aqueous sodium hydroxide solution. This solution was extracted with ethyl acetate (1×100 mL) and the ethyl acetate was discarded. The water layer was acidified to pH=3 by the addition of a 1N aqueous hydrochloric acid solution. The water layer was extracted with ethyl acetate (3×100 mL). The organic layers were combined, dried with sodium sulfate, filtered and concentrated under vacuum. The resulting solid was slurried in ethyl acetate (20 mL). Heptane (20 mL) was added to this mixture. The solvents were then concentrated under vacuum to a volume of approximately 20 mL. The solids were filtered and washed with a 1:1 ethyl acetate:heptane solution (2×10 mL). The solid was dried under high vacuum to afford [3,5-dibromo-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-proprionic acid (23) (553 mg, 72%) as an off-white solid; LRMS for C16H16Br2N2O4 (M+H) m/z=461. Molecular Weight=460.1249; Exact Mass=457.9477

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