تفاعل #1951056

معادلة التفاعل

4-fluorobenzyl bromide

trimethyl phosphite

→

(4-fluoro-benzyl)-phosphonic acid dimethyl ester

المردود 67.5%

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىat 90° C.
2. 2
   أخرىovernight
3. 3
   درجة الحرارةto cool to ambient temperature
4. 4
   غسيلThe solution was washed with saturated sodium bicarbonate (350 mL)
5. 5
   تجفيفThe organic phase was dried with magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated by rotatry evaporation
8. 8
   أخرىThe resulting crude product was purified by flash silica chromatrography

الإجراء التجريبي

4-fluorobenzyl bromide (25 mL, 0.20 mol) was added to a stirred solution of trimethyl phosphite (35.9 mL, 0.30 mol) at ambient temperature, under a nitrogen atmosphere. The resulting solution was heated at 110° C. for six hours, and then at 90° C. overnight. The reaction mixture was allowed to cool to ambient temperature and then ethyl acetate (350 mL) was added. The solution was washed with saturated sodium bicarbonate (350 mL) and then with saturated brine (2×350 mL). The organic phase was dried with magnesium sulfate, filtered, and concentrated by rotatry evaporation. The resulting crude product was purified by flash silica chromatrography using 0-35% acetonitrile in ethyl acetate as eluant to yield (4-fluoro-benzyl)-phosphonic acid dimethyl ester (29.44 g, 135 mmol, 66% yield) as a colorless oil. 1H NMR (400 MHz, DMSO) δ 7.33-7.28 (m, 2H); 7.17-7.12 (dd, 2H); 3.61-3.58 (d, 6H); 3.31-3.24 (d, 2H); ESMS (m/z): (M+1)+ found, 219.

المصدر