Water → 2-(Bromomethyl)acrylic acid ethyl ester

Phosphorus tribromide (17.16 g, 63.41 mmol) was added to a stirred solution of the compound of example 30 (17.92 g, 138.1 mmol) in dry ether (132 mL) at −10° C. The temperature was allowed to rise to 20° C. and stirring was continued for 3 h. Water (80 mL) was then added at −10° C. and the mixture was extracted with hexane (3×45 mL). The organic extracts were washed with saturated sodium chloride solution (2×45 mL) and dried with anhydrous MgSO4. Evaporation of solvent under vacuum gave 15.07 g (yield 56.6%) of the crude product, which was used directly in the next reaction without any further purification. 1H NMR (CDCl3, 400 MHz) δ 6.25 (s, 1H), 5.88 (s, 1H), 4.2 (q, 2H), 4.11 (s, 2H), 1.25 (t, 3H); 13C NMR (CDCl3, 400 MHz) 166.7, 140.1, 125.3, 61.1, 53.9, 14.4.

1. customto rise to 20° C.
2. extractionthe mixture was extracted with hexane (3×45 mL)
3. washThe organic extracts were washed with saturated sodium chloride solution (2×45 mL)
4. dry with materialdried with anhydrous MgSO4
5. customEvaporation of solvent under vacuum

ORD record

ord-2bb098052c6841f0b1e1da19565476ff

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07365091B2