Methyl iodide → {2-[4-(4-Fluoro-phenoxy)-phenyl]-ethyl}-methyl-carbamic acid tert-butyl ester

{2-[4-(4-fluoro-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (3.018 mmol, 1 eq) was dissolved in dry THF (30 ml) and NaH (3.621 mmol, 1.2 eq) was added. After 30 min, the reaction mixture was treated with methyl iodide (30.176 mmol, 10 eq) and was stirred overnight. After overnight the excess NaH was quenched by a slow addition of water, diluted with brine (30 ml) and extracted with Et2O (3×20 ml). Combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated to give a product without further purification {2-[4-(4-fluoro-phenoxy)-phenyl]-ethyl}-methyl-carbamic acid tert-butyl ester (1.592 mmol, yield=53%, purity=97%). [M+H]+=272.28 1H NMR (300 MHz, CDCl3) δ/ppm 1.55 (s, 9H), 7.24 (m, 5H), 3.39 (br. s., 2H), 6.83-7.03 (m, 5H), 7.06-7.17 (m, 2H), 7.24 (s, 2H)

1. customAfter overnight the excess NaH was quenched by a slow addition of water
2. additiondiluted with brine (30 ml)
3. extractionextracted with Et2O (3×20 ml)
4. dry with materialCombined organic layers were dried over anhydrous Na2SO4
5. filtrationfiltered
6. customevaporated
7. customto give a product

ORD record

ord-d788ace6d0c44a8a9397a5daffd81c2b

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174968B2