反応 #1605814

反応方程式

2-Phenyl-4-bromoaniline

tert-butyl-3-butenoate

tri-(o-tolyl)phosphine

diisopropylethylamine

→

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

収率 78.8%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   ろ過the reaction mixture was filtered through celite
2. 2
   洗浄washed with ethyl acetate (120 mL)
3. 3
   洗浄The organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL)
4. 4
   乾燥dried over sodium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他The residue was purified by a silica gel column

実験手順

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).

出典