Oxalyl chloride → Ethyl 1-bromocyclopentane-1-carboxylate

DMF (a few drops) was added to a mixture of 1-bromocyclopentane-carboxylic 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-cabe685616a641b39449d464774354e7

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541592B2