반응 #1052821

반응 방정식

N-(2-chloro-3-formylphenyl)acetamide

4-bromo-1-chloro-2-(trifluoromethyl)benzene

NH4Cl

I2

→

(±)-N-[2-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]hydroxymethyl]phenyl]acetamide

수율 74.5%

용매

THF

THF

THF

반응 조건

후처리

1. 1
   온도cooled to 10° C
2. 2
   workup.STIRRINGThe mixture was stirred at RT for 3 hours
3. 3
   추출extracted with EtOAc
4. 4
   기타The organic layer was separated
5. 5
   기타dried
6. 6
   여과filtered
7. 7
   기타the solvent was evaporated
8. 8
   기타The residue was purified by column chromatography (eluent: CH2Cl2/CH3OH 98.5/1.5)
9. 9
   기타The pure fractions were collected
10. 10
    기타the solvent was evaporated

실험 절차

A solution of 4-bromo-1-chloro-2-(trifluoromethyl)benzene (0.165 mol) in THF (30 ml) was added dropwise under N2 flow to a suspension of Mg (0.181 mol) and a crystal of I2 in THF (20 ml). The mixture was stirred at 30-35° C. for 2.5 hours and then cooled to 10° C. The mixture was added dropwise at 5° C. under N2 flow to a solution of N-(2-chloro-3-formylphenyl)acetamide (0.0788 mol) in THF (500 ml). The mixture was stirred at RT for 3 hours, poured out into ice and NH4Cl, and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography (eluent: CH2Cl2/CH3OH 98.5/1.5). The pure fractions were collected and the solvent was evaporated, yielding 22.2 g (74%) of (±)-N-[2-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]hydroxymethyl]phenyl]acetamide (interm. 25).

출처