반응 #1605814

반응 방정식

2-Phenyl-4-bromoaniline

tert-butyl-3-butenoate

tri-(o-tolyl)phosphine

diisopropylethylamine

→

tert-butyl (3E)-4-(3-amino-4-phenylphenyl)-3-butenoate

수율 78.8%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   여과the reaction mixture was filtered through celite
2. 2
   세척washed with ethyl acetate (120 mL)
3. 3
   세척The organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL)
4. 4
   건조dried over sodium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was purified by a silica gel column

실험 절차

2-Phenyl-4-bromoaniline (564.7 mg, 2.28 mmol) was dissolved in N,N-dimethylformamide (25 mL) and, at room temperature, thereto were added tert-butyl-3-butenoate (582.5 mg, 4.10 mmol), tri-(o-tolyl)phosphine (1.87 g, 6.16 mmol), and diisopropylethylamine (0.78 mL, 4.56 mmol). The reaction mixture was deaerated, palladium acetate (67.4 mg, 0.30 mmol) was added, and the mixture was deaerated again. After stirring at 90° C. overnight, the reaction mixture was filtered through celite and washed with ethyl acetate (120 mL). The organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL), thereafter dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by a silica gel column to obtain tert-butyl (3E)-4-(3-amino-4-phenylphenyl)-3-butenoate (555.8 mg).

출처