Ammonia → 1-(4-Bromophenyl)cyclopropane-1-carboxamide

Temperature

-15 °C

To a −15° C. solution of 1-(4-bromophenyl)cyclopropanecarboxylic acid from Step 2 (1.5 g) in chloroform (60 mL) were slowly added isobutyl chloroformate (900 μL) and triethylamine (1.1 mL). The reaction mixture was stirred at −15° C. for 2 hours. Then it was saturated with ammonia gas and stirred at −15° C. for 10 minutes. The reaction mixture was allowed to stand at room temperature for 1 hour then poured into water (60 mL) and partitioned. The aqueous layer was extracted with dichloromethane (2×160 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by swish using diethyl ether and hexanes to yield the title compound.

1. customTo a −15° C.
2. stirringstirred at −15° C. for 10 minutes
3. waitto stand at room temperature for 1 hour
4. custompartitioned
5. extractionThe aqueous layer was extracted with dichloromethane (2×160 mL)
6. washThe combined extracts were washed with brine
7. dry with materialdried with magnesium sulfate
8. customthe solvent removed in vacuo
9. customThe residue was purified

ORD record

ord-931745d160ab4db0917cab30160d825e

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687524B2