Ethyl Bromide → HCID 58951694, compound

Temperature

0 °C

A solution of 2-(3-chlorophenyl)acetonitrile (10.00 g, 66 mmol) and ethyl bromide (4.9 mL, 66 mmol) in DMSO (25 mL) was added dropwise to a stirred solution of NaH (60% dispersion in mineral oil (2.6 g, 66 mmol)) in DMSO (75 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred for 30 minutes at 0° C. and then brought to room temperature and stirred for 23 hours. The reaction mixture was carefully quenched with water, and was then diluted with EtOAc. The organic layer was separated, washed with water (2×) and brine, dried (MgSO4), and concentrated in vacuo to give the crude product as an orange oil. The crude oil was purified by silica flash chromatography (0-5% EtOAc/hexane) to give the desired compound as a colorless oil (4.69 g).

1. custombrought to room temperature
2. stirringstirred for 23 hours
3. customThe reaction mixture was carefully quenched with water
4. additionwas then diluted with EtOAc
5. customThe organic layer was separated
6. washwashed with water (2×) and brine
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo
9. customto give the crude product as an orange oil
10. customThe crude oil was purified by silica flash chromatography (0-5% EtOAc/hexane)

ORD record

ord-e3810c26c4aa4f368fbb6841a479a5b8

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07635715B2