Oxalyl chloride → Ethyl 1-bromocyclopentane-1-carboxylate

DMF (a few drops) was added to a mixture of 1-bromocyclopentanecarboxylic acid (23.9 g, 124 mmol) and oxalyl chloride (11.6 mL, 130 mmol) in 250 mL of CH2Cl2. The mixture was stirred at ambient temperature for 2 h. After removing the low-boiling solvents in vacuo, ethanol (50 mL) was added to the residue followed by the addition of N,N-diisopropylethylamine (22.7 mL, 130 mmol). The mixture was stirred at ambient temperature for 20 min. After removing the low-boiling solvents in vacuo, the residue was partitioned between diethyl ether and water. The organic portion was washed with water and brine, and conc. in vacuo. The crude product was filtered through a plug of silica gel using 0 to 10% EtOAc in hexanes as the eluant. The title compound was obtained as a pale oil.

1. customAfter removing the low-boiling solvents in vacuo, ethanol (50 mL)
2. additionwas added to the residue
3. stirringThe mixture was stirred at ambient temperature for 20 min
4. customAfter removing the low-boiling solvents in vacuo
5. customthe residue was partitioned between diethyl ether and water
6. washThe organic portion was washed with water and brine
7. filtrationThe crude product was filtered through a plug of silica gel using 0 to 10% EtOAc in hexanes as the eluant

ORD record

ord-a81deba6fbbe4eee8285d8bc265b95ef

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07253196B2