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22.7.6.1.2 Method 2: Substitution of Halogens

DOI: 10.1055/sos-SD-022-00923

Kantlehner, W.Science of Synthesis, (200522796.

Chloro(difluoro)methane, dichloro(fluoro)methane, and chloroform react with the sodium salts of N-alkylanilines in 1,2-dimethoxyethane to give N,N,N-trialkyl-N,N,N-tri­aryl-substituted ortho amide derivatives 7 (Scheme 2).[‌10‌,‌11‌] The reaction proceeds via di­halocarbenes. Chloro(difluoro)methane (6) is the preferred substrate since its use gives cleaner products with higher yields. Typically the isolated products are obtained after filtration and washing with water.

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Meeeeeeeeee 8

M8 Me8 Meeee (%) Mee
Me Me 88 [‌88‌]
Me Me 88 [‌88‌]
Me 8-M8MM8M8 88 [‌88‌]

Meeee eeeeee 8 eee ee eeeeeeee ee eeeeee eeeeee ee eeeeeeeeee ee eeeeeee eeee eeeeeeeee eeeeee ee eeeeeeee ee eee eeeeeeee ee eeeeee eeeeeeeee (Meeeee 8).[‌88‌] Mee eeeeee eeeee eeeeeeeeeeee eee eeeeee eeee eeee e eeeeee eeeeeee eeeee eeee eeeeeeee. Mee eeeeeeee eee eeee ee eeeeeeeee eeee e eeeeeeeeee ee eeeeee eeeeeeeee ee e eeeeeee ee eeeeeee eeeee eee eeeee, eeeeeeee eee eeeeee eee eeeeeee eeeee eeeeeee eeee eeeeeeeeee eee eeeeee ee eeeeeeeeee. Meeeeeeee eee eeeeeeee eee eeeeeeee eeeee eeeeeeeeee eeeeeeeeeeee ee eeeeeeeeee.

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Meeeeeeeeee 8

M8 M8 Meeee (%) Mee
(MM8)8 88 [‌88‌]
(MM8)8 88e [‌88‌]
(MM8)8M(MM8)8 88e [‌88‌]
(MM8)8MMe(MM8)8 88 [‌88‌]
Me Me 88 [‌88‌]

e Mee eeeee eeeee eeeeeeeeeee eeeeeeee ee eeeee eeeeeee eeeeeeeee eeee ee eeeeee eeee ee eeeeee ee eee eeeeeeeeeeeee eeeee ee eeeeeee eeeee eeeeeeeeeeeeee ee eee eeeee eeeee.

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Meeeee 8 Mee Meeeeeeee ee Meeeeeeeeeee Meeee Meeeee eeee Meeeeeeeee[‌88‌‌88‌]

Mee eeeee eeeee eeeeeeeee ee eeeeeeeeee ee eeeeeeeeee eeeeeeeee eeeeeeeeeeee ee eeeeeeeee ee eee eeeeeeee eeeeeeee ee eee eeeeeeeeeeee eeeeeeeee.[‌88‌] Me eee eeeeeeee ee eeeeeeeeeeeeeee (eeeeeeee eeee MMMe8, MeMM, eee Me8MMe) eeee eeeeeeeeeeeee 88 (M8=e-Me, 8-eeeeeeeee), eee eeeeeeee eeeee ee eee eeeeeeeeeeeee 8-(eeeeeeeeeeeeee)-8M-eeeeeeeeeeeeee 88 (Meeeee 8);[‌88‌] eeeee eee eeeeee eeeeeeeeee eeee eeeee eeeeee eee eeeeeeee eeeee eeee eeeeeeeeee.[‌88‌]

Meeeee 8 Meeeeeeeeee ee Meeee Meeee Meeeeeeee eeee Meeee Meeeeeeeee Meeeeeee Meeeeeeeee[‌88‌]

Me eeeeeeee, eeeeeeeee eeeeeeeeee ee eeeee eeeeeeee eeeeeeeee, eeeee ee eeeeee eeeeeeeeee ee eeeeeeee eeeee, eeeeeee eeeee eeeeee eeeee eeeee-eeeeeeee eeeeeeeee eeeeeeeeee.[‌88‌] Meeeeeeeeeeeeee eee eeee ee eeeeeeee ee eeeeeeeeeee ee eeeeee eeeeeeeeeeeeeeee. Meee ee ee eeeeeeeee eeee eee ee eee eeeee eeee eeeeeeee ee eeeeeeeeeeee eeeeee ee eeee eee eeeeeeeeeeeee eeeee eeeeee (Meeeee 8);[‌88‌,‌88‌,‌88‌,‌88‌] eeeeeee, eee eeeeee eee eee, e.e. eeee(eeeeeeeeeeeee)eeeeeee (88) eee eeeeeeee ee 88% eeeee.[‌88‌,‌88‌,‌88‌,‌88‌,‌88‌,‌88‌,‌88‌]

Meeeee 8 Mee Meeeeeee ee Meeeeeee eee Meeeeeeeeeee Meeeee eeee Meeeee Meeeeeeeeeeeeeee[‌88‌,‌88‌,‌88‌,‌88‌,‌88‌,‌88‌,‌88‌]

Meee M-eeeeeeeeeee eeeee eee eeeeeee eeee eeeeeeeeee eee eeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeee, eeeee eeeeee eeee eee eeeeee eeeeee eeeeee eeeee eee eeeeeeee. Me eee eeeee eeee eeeeeeeeee eee eeeeee (ee eeeeeeeeeee ee eee eeee); eeeee eeeeeeeeee eeeee eeee eeeeeeeeeeeeeee ee eeee eee eeeee eeeeee.[‌88‌] Mee eeeeee eee eeeeeeee ee eeee eeeeeeeeee eee eeee.

Mee eeee eeeeee eeeee ee eeeeeeee eeeeeeeee eee eeeeeee ee eeeeeeee eeee eeeeeeeeeeeeeee [eeeeeeee eeee eeeeee(eeeeeeee)eeeeeee]. Mee eeeeeeeeeee eeeee eeeeeeee 88 eee ee eeeeeeeeeee ee eee eeeee eeeee eeeeeeeeee 88 (Meeeee 8), eeeeeeee eee eeeeeeee eeeee eeee eeeeee eeeeeeeee.[‌88‌]

Meeeee 8 Meeeeeee ee e Meeeeeeeeee Meeee Meeeeeee eeee Meeeeeeeeeeeeee[‌88‌]

Meeeeeeee ee eeeeeeee(eeeeeeeeeeee)eeeeeee eeee eee eeeeeeeee eee eeeeee eeeee ee eeeeeeeeeee eee eeeeeeeee, eeeeeeeeeeee, eeeeeeee eee eeeee eeeee eeeeeeeeeee 88 eee 88 (Meeeee 8).[‌88‌] Mee eeeeeeee eeeeeeee eee eee eeeeeeeeeeeeeee eeeeeeee eeeee eee eeeeeeee eee eeeeeeee ee eee ee eeeeee eeeeee.

Meeeee 8 Meeeeeeee ee Meeeeeeeeee- eee Meeeeeeee-Meeeeeeeeee Meeee Meeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8,8-[(Meeeeeeeeeeee)eeeeeeeee]eee[8M-eeeeeeeee-8,8(8M)-eeeee] (88):[‌88‌]

Me e eeeeeeeeee ee eeeeeeeee 8,8-eeeee-8,8-eeeeeeeeeeeeeee-8-eee (88.8e, 8.88eee) ee eee MMMe8 (888eM) eee eeeee eeeeeeee(eeeeeeeeeeee)eeeeeee (88.8e, 8.88eee) ee eee MMMe8 (88eM) eeeeeeee eeee eeeeeeee eee eeeeeeeee ee eeeeeeee. Mee eeeeeee eeeeee eeee eee eee eeeeee ee 88°M. Meeee 8e ee eeeeeeee ee 88°M eee eeeeeeeee eeeee eee eeeeeee eee eeeeeee eeee eee ee MeMM. Mee eeeeeeeee eeeeeeee eeee eeeeee eeee MeMM eee Me8M, eee eeeeeeeeeeeeee (MMM) ee eeeeeee e eeeeeeeee eeeeeeeeeeeeeeee eeeeeeee; eeeee: 88.8e (88%).

References


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