Ethylene Glycol → 2-HYDROXYETHYL 2-BROMOISOBUTYRATE

Anhydrous ethylene glycol (301.3 g, 4.85 mol) and triethylamine (28 mL, 200 mmol) were diluted with dry tetrahydrofuran (100 mL). The reaction mixture was cooled in an ice-water bath and a solution of α-bromoisobutyryl bromide (12 mL, 97.1 mmol) in dry tetrahydrofuran (50 mL) was slowly added while stirring. The mixture was stirred in the cooling bath for 1 h and then at room temperature for 16 h. The reaction mixture was then poured into water (800 mL) and extracted with dichloromethane (6×100 mL). The organic fractions were combined, washed with acidic water (pH=4), dried over MgSO4 and evaporated to dryness to afford 17.477 g (yield=85.3%) of a very pale yellow liquid. 1H NMR (CDCl3, δ, ppm): 4.30-4.19 (m, 2H), 3.86-3.75 (m, 2H), 2.86-2.47 (broad peak, 1H, OH), 1.89 (s, 6H). 13C NMR (CDCl3, δ): 171.95, 67.40, 60.63, 55.89, 30.72.

1. temperatureThe reaction mixture was cooled in an ice-water bath
2. stirringThe mixture was stirred in the cooling bath for 1 h
3. extractionextracted with dichloromethane (6×100 mL)
4. washwashed with acidic water (pH=4)
5. dry with materialdried over MgSO4
6. customevaporated to dryness
7. customto afford 17.477 g (yield=85.3%) of a very pale yellow liquid

ORD record

ord-41b8f61f722b45d59749807dd79976b5

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445610B2