TERT-BUTYL 5-BROMO-2-FLUOROBENZYLCARBAMATE synthesis

Yield:491836-84-1 100%

Reaction Conditions:

with sodium hydroxide in 1,4-dioxane;water;

Steps:

37

Dissolve 5-bromo-2-fluorobenzylamine hydrochloride (1. 00 g, 4. 16 mmol) in 1, 4- dioxane (16 mL) and 0. 5 N sodium hydroxide (10 mL). Add di-tert-butyl dicarbonate (1. 09 g, 4. 99 mmol) and stir the biphasic mixture overnight. Make the aqueous layer acidic with aqueous saturated solution of sodium hydrogensulfate and extract three times with ethyl acetate. Combine the organic layers and wash with an aqueous saturated solution of sodium chloride, dry (sodium sulfate), filter, and concentrate to give the title compound as a colorless oil, which crystallizes upon standing (1. 3 g, 100%). 1HNMR (400 MHz, DMSO-d6) 6 1. 35 (s, 9H), 4. 11 (d, J = 5. 7 Hz, 2H), 7. 12 (dd, J = 9. 7, 8. 8 Hz, 1H), 7. 46-7. 38 (m, 2H).

References:

WO2005/94822,2005,A1 Location in patent:Page/Page column 42-43