반응 #657251

반응 방정식

ammonium chloride

n-butyllithium

19

5,7-Dibromo-2,3-dihydrobenzofuran

N,N-dimethylformamide

→

crystals

수율 27.1%

5-Bromo-2,3-dihydrobenzofuran-7-carbaldehyde

수율 27.1%

용매

THF

반응 조건

후처리

1. 1
   기타was degassed at −78° C.
2. 2
   기타The solvent was removed
3. 3
   세척washed with water (3×50 mL)
4. 4
   건조then dried with anhydrous sodium sulfate
5. 5
   기타Solvent removal

실험 절차

A sample of 19 (6.0 g, 26.5 mmol) in freshly distilled dry THF was degassed at −78° C. and n-butyllithium (25 mL of 1.05 M, 26 mmol) was added dropwise by syringe. Then N,N-dimethylformamide (2.9 mL, 26 mmol) was added dropwise via syringe. The reaction mixture was allowed to come to room temperature overnight. Saturated ammonium chloride (10 mL) was added to and the mixture was stirred for 30 minutes. The solvent was removed and the residue was taken up in dichloromethane (50 mL), and washed with water (3×50 mL) then dried with anhydrous sodium sulfate. Solvent removal yielded yellow crystals (1.6 g) which were washed with ether and recrystallized from a minimum of hot methanol to give white crystals of 20 (1.32 g, 22%) mp=99-100° C.

출처