تفاعل #42469

معادلة التفاعل

methyl 3,5-dibromo-4-methoxybenzoate

BINAP

cesium carbonate

butylamine

→

title compound

Methyl 3-bromo-5-(butylamino)-4-methoxybenzoate

المذيبات

toluene

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was refluxed overnight
2. 2
   درجة الحرارةThe mixture was cooled to room temperature
3. 3
   ترشيحfiltered through diatomaceous earth
4. 4
   تركيزconcentrated under reduced pressure
5. 5
   أخرىPurification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes)

الإجراء التجريبي

To a stirred solution of Pd(OAc)2 (144 mg), BINAP (1.2 g), and cesium carbonate (8.4 g) in toluene (100 mL) was added butylamine (1.6 mL), and the mixture was heated at 80° C. for 15 min. A solution methyl 3,5-dibromo-4-methoxybenzoate (4.2 g) in toluene (30 mL) was added dropwise over 20 min. The mixture was refluxed overnight. The mixture was cooled to room temperature, filtered through diatomaceous earth, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes) provided 3.5 g of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.52, 7.19, 3.90, 3.88, 3.18, 1.66, 1.46, 0.97.

المصدر