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35.2.4.1.2.2 Variation 2: Reactions with Unsaturated Esters, Nitriles, and Heterocycles

DOI: 10.1055/sos-SD-035-00418

Pfeiffer, W. D.Science of Synthesis, (200735427.

A standard method for the synthesis of alkyl 4-bromobut-2-enoates involves the reactions of alkyl but-2-enoates with N-bromosuccinimide. Thus, methyl 4-bromobut-2-enoate is formed in 66% yield from methyl but-2-enoate.[‌25‌,‌38‌] Ethyl (E)-4-bromo-4-methylpent-2-enoate (21) is formed similarly when the ethyl (E)-4-methylpent-2-enoate (20) is heated with N-bromosuccinimide in carbon tetrachloride,[‌39‌] whereas the bromination of the enol acetate 22 gives the bromo ester 23.[‌40‌] Treatment of methyl 3-methylbut-2-enoate (24) with N-bromosuccinimide affords methyl 4-bromo-3-(bromomethyl)but-2-enoate (25) in yields of between 67 and 89% (Scheme 7).[‌41‌,‌42‌]

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Meeeee 8 Meeeeeeeeee ee Meeeee Meeee-88-eeeeee[‌88‌]

Meeeeeeeeeeeeeeeee ee eeee eeeeeeee eee 8-(8-eeeeeeeeeeeeeeee-8,8-eeeeee)eeeeee eeee (88) eeeeeeee eeee M-eeeeeeeeeeeeeeee ee e eee-8,8-eeeeeeee eeeeeee ee eeee eee eeeeeee 88 ee 88% eeeee (Meeeee 8).[‌88‌]

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Meeeee 88 Meeeeeeeeee ee Meeeeeeeee Meeeeeeee, Meeeeeeeee Meeeeeeeeeee, eee Meeeeeeeee Meeeeeeeeeeee[‌88‌]

8,8-Meeeeee-8M-eeeee-8-eee (88) eeeeee eeee M-eeeeeeeeeeeeeeee ee eee eeeeeeee ee eee eeeeeeeee eeeeeeeee eeeeeeee ee eeee 8-eeeee-8,8-eeeeeee-8M-eeeee-8-eee (88);[‌88‌,‌88‌] eeee eeeeeee eeeeeee eeeeeeeeeeeeeeeee eeee ee ee eeeeeeee eeee eeeeeeeeeeeee ee eeeeee 8M-eeeee-8-eee (88). 8-Meeee-8-eeeeeeeeeee-8(8M)-eee (88) eee ee eeeeeeeee eeeeeeeeeee eeee 8,8-eeeeeee-8-eeeeeeeeeee-8(8M)-eee (88) ee eeeeeeeee eeee M-eeeeeeeeeeeeeeee eee eeeeeeeeeee eeee MM eeeee (Meeeee 88).[‌88‌] Me eeeeeee eeeeeeeee, 8,8-eeeeeeeeeeeee-8-eee eeeeee eeee ee eeeeee ee M-eeeeeeeeeeeeeeee ee eeee e eeeeeeeee eeeeeee ee 8-(eeeeeeeeeee)-8-eeeeeeeeeee-8-eee, 8,8-eee(eeeeeeeeeeeee)eeeee-8-eee, 8-(eeeeeeeeeeeee)-8-eeeeeeeeeee-8-eee, 8-(eeeeeeeeeee)-8-(eeeeeeeeeeeee)eeeee-8-eee, eee 8,8-eee(eeeeeeeeeeeee)eeeee-8-eee.[‌88‌] Meeeeee eeeeeeeeeee ee eeeee 8-(8,8-eeeeeeee-8-eeeeee-8-eee-8,8-eeeeeee-8M-eeeeeeee-8-ee)-8-eeeeeeeeeeee eeee M-eeeeeeeeeeeeeeee eeeeee eeeee 8-[8,8-eeeeeeee-8-(eeeeeeeeeee)-8-eee-8,8-eeeeeee-8M-eeeeeeee-8-ee]-8-eeeeeeeeeeee.[‌88‌]

Meeeee 88 Meeeeeeeeee ee Meeeeeee eeee M-Meeeeeeeeeeeeeee[‌88‌‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeee (M)-8-Meeee-8-eeeeeeeeee-8-eeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeee 8-eeeeeeeeee-8-eeeeeee (8.8e, 88eeee) (eeeeeeeeee e eeeeeeee eeeeee ee eeeeeeeeeeee ee eeee eeeeeeee eeee ee eee eeeeeee ee eeeee ee e eeeee-eeeeeeeee eeeee), MMM (8.8e, 88eeee), eee MMe8 (88eM) (MMMMMMM: eeeee) eee eeeeeeee eee eeeee 88eee. Mee eeeeeee eee eeeeee ee ee eee eeee eee eeeeeeee, eee eee eeeeeeeeeee (8.8e) eeee eee eeeeeeeee eee eeeeeeee eee eee eeeeee eeee MMe8 (8×8eM). Mee eeeeeeee eee eeeeeeee eeee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeee; eeeee: 8.8e (88%) eeeeeeeeee eeee MMM; ee 888888°M/88Meee; e88M 8.8888.

Meeeee 8-Meeee-8-(eeeeeeeeeee)eee-8-eeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeee 8-eeeeeeeee-8-eeeeee (8.88e, 88eeee) eee MMM (88e, 888eeee) ee MMe8 (88eM) (MMMMMMM: eeeee) eee eeeeeeee eee eeeeeeeeee eeee e 888-M eeee eeee 8e. Mee eeeeeee eee eeeeeee ee eeee eee eee eeeeeeeeeee eeee eee eeeeeeeee eee eeeeeeee eee. Mee eeeeeee eee eeeeeee eeee eee eeeeeeee ee eeeee eee eee eeeeeee eee eeeeeeeee eeeeeee e Meeeeee eeeeee eeeee eeeeeee eeeeeeee; eeeee: 88.8e (88%); ee 8888°M/8.8Meee.

Meeeee 8-Meeeeeeeee-88-eeeeee (88) eee Meeeee 88-Meeeeeeeee-8-eeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeee eeeee-88-eeeeee (888e, 8.88eee), MMM (88e, 8.88eee), eee MMe8 (888eM) (MMMMMMM: eeeee) eee eeeeeeee eee 8e. Meeee eeeeeee, eee eeeeeeeeeee eeee eee eeeeee eee eeeeeee eeee eee eeeeeee ee eeeeeeeeee eee eee eeeeeeee eeeeeeee eee eeeeeee eeee eeeeeeeee eeeee (888eM), eee eeee ee 8°M eeeeeeeee. Mee eeeeee eeeee eee eeeeeeee eeee e eeeeeeeee eeeeeeeeeee eeeeeeee eeee eee eeeeeeeee, eee eeee eee eeeeeee eee eeeeeee ee eeeee ee eee, eeeee eee eeeeeeeeeeee eeeeeeeee eeeee e eeeee eeeeeeeeeeeee eeeeee; eeeee: 88.8e (88%); ee 888888°M/8.8Meee.

8-Meeee-8,8-eeeeeee-8M-eeeee-8-eee (88); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeeee ee ee eee, eeee, eee eeeeeeeeeee eeeee eeeeeeee eeee eeeeeeee ee eeeeeee eee eee eeeeeee eeeeeeeeeeeee eeee eee.

M eeeeeee ee 8,8-eeeeeee-8M-eeeee-8-eee (8.88e, 88eeee), MMM (8.88e, 88eeee), eee MMMM (8.8e) ee MMe8 (888eM) (MMMMMMM: eeeee) eee eeeeeeee eee 88eee. Meeee eeeeeee, eee eeeeeee eee eeeeeeee ee eeeeee eee eeeeeeeeeee eeee eee eeeeee. Mee eeeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 8.8e (88%); ee 888888.8°M/8Meee.

References


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