Réaction #2487416

Équation de réaction

Hydroquinone monomethyl ether

2-Bromopropionyl bromide

2-hydroxyethyl methacrylate

triethylamine

→

oil

Rendement 63.9%

2-((2-bromopropanoyl)oxy)ethyl methacrylate

Rendement 63.9%

Solvants

ethyl acetate

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Filtrationfiltered
2. 2
   workup.ADDITIONfurther treated with more MEHQ (˜15 mg)
3. 3
   Autreevaporated to dryness

Mode opératoire

2-Bromopropionyl bromide (18 g, 0.083 mol, 1 m.e) in ethyl acetate (30 mL) was added dropwise to a mixture of 2-hydroxyethyl methacrylate (HEMA) (16.26 g, 0.125 mol, 1.5 m.e) and triethylamine (9.26 g, 0.091 mol, 1.1 m.e) in ethyl acetate (80 mL) at 0° C. under a N2 environment. Hydroquinone monomethyl ether (MEHQ) was added as an inhibitor at this stage (−15 mg, 1.2×10−4 mol). The reaction mixture was stirred overnight, then filtered, further treated with more MEHQ (˜15 mg) and then evaporated to dryness to give a clear colourless oil (14 g, 0.053 mol, 63% yield). 1H NMR (200 MHz, CDCl3) δ 1.82 (d, J=8 Hz, 3H, CH3CH—), 1.95 (s, 3H, (CH3CCO—), 4.36-4.46 (m, 5H, 2× —CH2O— and —CHBr), 5.60 (br. s, 1H, vinyl), 6.13 (s, 1H, vinyl) ppm.

Source