반응 #1558373

반응 방정식

Pyridinium tribromide

1-(6-(4-acetylphenyl)quinolin-2-yl)ethanone

HBr

→

2-bromo-1-(6-(4-(2-bromoacetyl)phenyl)quinolin-2-yl)ethanone

수율 77.6%

용매

acetic acid

반응 조건

후처리

1. 1
   농축The reaction was concentrated under vacuum
2. 2
   기타the residue was partitioned between aq NaHCO3 (15 mL) and EtOAc (30 mL+10 mL+10 mL)
3. 3
   세척washed with brine
4. 4
   기타dried
5. 5
   여과filtered
6. 6
   농축concentrated

실험 절차

Pyridinium tribromide (221 mg, 0.691 mmol) was added to a suspension of 1-(6-(4-acetylphenyl)quinolin-2-yl)ethanone (100 mg, 0.346 mmol) and HBr (0.061 mL, 0.35 mmol) in acetic acid (3 mL) the reaction mixture was stirred at 70° C.) for 6 h. The reaction was concentrated under vacuum and the residue was partitioned between aq NaHCO3 (15 mL) and EtOAc (30 mL+10 mL+10 mL). The organic layers were combined, washed with brine, dried, filtered and concentrated to yield crude 2-bromo-1-(6-(4-(2-bromoacetyl)phenyl)quinolin-2-yl)ethanone (120 mg) as white solid. LC-MS retention time 4.138 min; m/z 448.01 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® Luna 3u C18 2.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 0.8 mL/min, a gradient of 100% Solvent A/0% Solvent B to 0% Solvent A/100% Solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where Solvent A was 10% MeOH/90% H2O/0.1% trifluoroacetic acid and Solvent B was 10% H2O/90% MeOH/0.1% trifluoroacetic acid. MS data was determined using a MICROMASS® Platform for LC in electrospray mode.

출처