반응 #1543475

반응 방정식

I2

3-(4-benzyloxyphenoxy)benzo[b]thiophene

n-butyllithium

→

2-iodo-3-(4-benzyloxyphenoxy)benzo[b]thiophene

수율 86.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONUpon completion of the addition
2. 2
   온도to slowly warm to room temperature
3. 3
   기타The reaction was quenched by the addition of 0.1N sodium sulfite solution (200 mL)
4. 4
   기타The layers were separated
5. 5
   추출the aqueous extracted with ethyl acetate (2×150 mL)
6. 6
   건조dried (sodium sulfate)
7. 7
   농축concentrated in vacuo
8. 8
   기타to give an oil that
9. 9
   기타crystallized
10. 10
    기타Recrystallization from hexanes/ethyl ether

실험 절차

To a solution of 3-(4-benzyloxyphenoxy)benzo[b]thiophene (6.00 g, 18.1 mmol) in anhydrous tetrahydrofuran (100 mL) under N2 at -78° C. was added n-butyllithium (12.4 mL, 19.9 mmol, 1.6M in hexanes) dropwise via syringe. The solution turned from colorless to deep orange. After stirring for 20 minutes at -78° C., the lithio species was treated with I2 (5.03, 19.9 mmol), added dropwise via canula as a solution in 50 mL of anhydrous tetrahydrofuran. Upon completion of the addition, the reaction turned light yellow in color, and was allowed to slowly warm to room temperature. The reaction was quenched by the addition of 0.1N sodium sulfite solution (200 mL). The layers were separated and the aqueous extracted with ethyl acetate (2×150 mL). The organic layers were combined, dried (sodium sulfate), and concentrated in vacuo to give an oil that crystallized on standing. Recrystallization from hexanes/ethyl ether yielded 7.10 g (86%) of 2-iodo-3-(4-benzyloxyphenoxy)benzo[b]thiophene as a white crystalline powder. mp 87°-92° C. 1H NMR (CDCl3) d 7.72 (d, J=8.1 Hz, 1H), 7.47-7.20 (m, 8H), 6.89 (s, 4H), 5.01 (s, 2H). Anal. Calcd. for C21H15O2SI: C, 55.03; H, 3.30. Found: C, 55.29; H, 3.31.

출처