Methyl iodide → tert-butyl N-[(4-bromophenyl)methyl]-N-methylcarbamate

Temperature

50 °C

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).

1. filtrationThe reaction mixture was filtered through a bed of celite
2. washthe celite was washed with methanol (2×20 mL) and dichloromethane (2×20 mL)
3. concentrationThe filtrate was concentrated
4. customto remove most of the DMF
5. additionThe residue was treated with water (50 mL)
6. customa white emulsion formed
7. extractionThis mixture was extracted with ethyl acetate (4×25 mL)
8. dry with materialdried over Na2SO4
9. customthe solvent was evaporated

ORD record

ord-e81bcb87f3e04374b44a18f1c4a32773

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07956052B2