2-Bromoethanol → 2-Bromoethyl 2,2-dimethylpropanoate

2,2-Dimethylpropionyl chloride (10 mL, 81.2 mmol) was added over 10 min to an ice-cooled solution of 2-bromoethanol (5.48 mL, 77.4 mmol) and DIPEA (20.8 mL, 121.8 mmol) in DCM (150 mL). The reaction mixture was stirred in the ice bath for a further 15 min, then at RT for 16 h. The reaction mixture was washed successively with 1M HCl, saturated aqueous NaHCO3 and water. The organic fraction was dried (Na2SO4) then concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, eluant 1-6% EtOAc in cyclohexane) affording the title compound as a colourless oil (10.58 g, 65%). 1H NMR (CDCl3, 300 MHz): 4.37 (2H, t, J=6.0 Hz), 3.52 (2H, t, J=6.0 Hz), 1.23 (9H, s).

1. washThe reaction mixture was washed successively with 1M HCl, saturated aqueous NaHCO3 and water
2. dry with materialThe organic fraction was dried (Na2SO4)
3. concentrationthen concentrated in vacuo
4. customThe resulting residue was purified by column chromatography (Si—PCC, eluant 1-6% EtOAc in cyclohexane)

ORD record

ord-80ef3a45e2ac4a0db168c224177f736f

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653089B2