تفاعل #488746

معادلة التفاعل

tert-butyl-4-bromobenzylcarbamate

CH3I

→

tert-butyl-4-bromobenzyl(methyl)carbamate

المردود 99.1%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe reaction mixture was filtered through a bed of celite
2. 2
   غسيلthe celite was washed with methanol (2×20 mL) and dichloromethane (2×20 mL)
3. 3
   تركيزThe filtrate was concentrated
4. 4
   أخرىto remove most of the DMF
5. 5
   workup.ADDITIONThe residue was treated with water (50 mL)
6. 6
   أخرىa white emulsion formed
7. 7
   استخلاصThis mixture was extracted with ethyl acetate (4×25 mL)
8. 8
   تجفيفdried over Na2SO4
9. 9
   أخرىthe solvent was evaporated

الإجراء التجريبي

In a 60-mL vial, tert-butyl-4-bromobenzylcarbamate (1.25 g, 4.37 mmol) was dissolved in DMF (12 mL). To this solution was added Ag2O (4.0 g, 17 mmol) followed by the addition of CH3I (0.68 mL, 11 mmol). The mixture was stirred at 50° C. for 18 hours. The reaction mixture was filtered through a bed of celite and the celite was washed with methanol (2×20 mL) and dichloromethane (2×20 mL). The filtrate was concentrated to remove most of the DMF. The residue was treated with water (50 mL) and a white emulsion formed. This mixture was extracted with ethyl acetate (4×25 mL), dried over Na2SO4, and the solvent was evaporated to yield tert-butyl-4-bromobenzyl(methyl)carbamate (1.3 g, 98%) as a yellow oil. 1H NMR (300 MHz, DMSO-d6) δ 7.53 (d, J=8.1 Hz, 2H), 7.15 (d, J=8.4 Hz, 2H), 4.32 (s, 2H), 2.74 (s, 3H), 1.38 (s, 9H).

المصدر