반응 #1929087

반응 방정식

bromoacetylbromide

13

Tetramethyl 1-(4-aminobenzyl)methylenebisphosphonate

pyridine

→

14

수율 68.2%

Tetramethyl 1-(4-bromoacetamidobenzyl)methylenebisphosphonate

수율 68.2%

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGthe resulting mixture was stirred for 4 h at that temperature
2. 2
   기타The reaction was quenched by the addition of water
3. 3
   추출the product was extracted with CH2Cl2
4. 4
   세척The combined organic layers were washed with brine
5. 5
   건조dried over sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The crude yellow solid was purified by silica gel chromatography

실험 절차

A solution of 13 (0.959 g, 2.87 mmol) and pyridine (349 μL, 4.31 mmol) in CH2Cl2 was cooled in an ice-bath while stirring. A solution of bromoacetylbromide (250 μL, 2.87 mmol) in CH2Cl2 (5 mL) was added drop-wise and the resulting mixture was stirred for 4 h at that temperature. The reaction was quenched by the addition of water and the product was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude yellow solid was purified by silica gel chromatography resulting in 14 as a colorless solid (0.897 g, 67%). 1H NMR (400 MHz, CDCl3) δ 2.65 (tt, J=6.2, 24.4, 1H), 3.22 (dt, J=6.2, 17.4, 2H), 3.72 (d, J=3.7, 6H), 3.75 (d, J=3.7, 6H), 4.01 (s, 2H), 7.26 (d, J=8.6, 2H), 7.47 (d, J=8.6, 2H), 8.15 (bs, 1H): 31P (162 MHz, CDCl3) δ 26.33 (s, 2P).

출처