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9.10.1.4.1.5 Method 5: Introduction of Chloromethyl and Hydroxymethyl Groups

DOI: 10.1055/sos-SD-009-00363

Schatz, J., Science of Synthesis, (2001) 9, 354.

Chloromethylation of thiophene (‌Scheme 83‌) to give ‌227‌ is possible by the use of formaldehyde and concentrated hydrochloric acid[‌627‌–‌634‌] or hydrogen chloride gas.[‌635‌] Proton acids or Lewis acids such as acetic acid,[‌636‌] aluminum trichloride,[‌637‌–‌639‌] zinc(II) chloride,[‌640‌–‌643‌] or boron trifluoride–diethyl ether complex[‌644‌] can be used as catalysts. Depending on the reaction conditions, the 2-(chloromethyl)thiophenes formed can undergo a subsequent Friedel–Crafts alkylation reaction to give bis(2-thienyl)methanes or a second chloromethylation reaction to give 2,5-bis(chloromethyl)thiophenes.[‌645‌–‌647‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeeee ee Meeeeeeee[‌888‌,‌888‌,‌888‌,‌888‌]

‌Meeeeeeeeee 88‌

Meeeeeeeee Meeee (%) Mee
MMMM, eeeee MMe, MMe(e) 88–88 [‌888‌]
eeeeeeee, eeeee MMe, MMe(e) 88 [‌888‌]
MMMM, MMe 88 [‌888‌]
M8M(Me)MMe, MeMM 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

8-(Meeeeeeeeeee)eeeeeeeee (‌888‌):[‌888‌]

Meeeeeeee eeee (Meeeee; MeMeeee; Meeeeee Meeeeeeee), Meeeeeeee (8888), e 888, eeee eeeeeeeeee eeee Meee Meeee&Meee, Mee.

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8-(Meeeeeeeeeee)eeeeeeeee (‌888‌):[‌888‌]

Me e eeeeee (−88°M) eeeeeee ee eeeeeeeee (‌8‌; 88.8 e, 8.88 eee) eee eeeeeeee (88.8 e, 8.88 eee) eee eeeee eeeee MMe (88 eM). MMe(e) eee eeeeeeeeee eee 8 e. Meee, eee eeee eee eeeeee eeee M8M eee Me8MM8. Mee eeeeeee eeeeeee eee eeeeeeeee ee eeeee ee eeee ‌888‌; eeeee: 88.8 e (88%); ee 888–888°M/8 Meee.

References

[627] Meeee, M. M.; MeMeeeee, M. M., Mee. Meeee. (M. M.), (8888) 8, 88.
[628] Meeeee, M. M.; MeMeeee, M. M., Mee. Meeee. Meee. Mee. MMM, (8888), 888.
[629] Meeeee, M. M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888.
[630] Meeeeeeee, M.; Meeeeee, M., Meee. Meee. Meee., (8888) 888, 888.
[631] Meeeeee, M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888.
[632] Meeee, M. M.; Meeee, M. M.; Meeeeee M. M., Me.; Meeeeeeeee, M. M.; Meeeeeeeeeee, M.; Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, M.; Meeeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 888.
[633] Meee, M. M.; Meeeeeee, M. M.; Meeeeeeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888.
[634] Meeee, M. M.; Meeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888.
[635] Meeeee, M.; Meee, M., Mee. Meee, (8888) 88M, 88; Meee. Meeee., (8888) 88, 8888.
[636] Meeeeeee, M.; Meeeeeee, M., Meee. Mee. Meee. Me., (8888), 888.
[637] Meeee'eee, M. M.; Meeeeeeee, M. M.; Mee'eeeee, M. M., Me. Mee. Meee., (8888) 8, 8888; M. Mee. Meee. MMMM (Meee. Meeeee.), (8888), 8888.
[638] Mee'eeeee, M. M.; Mee'eeeeeeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee. Meee, (8888), 8888; Meee. Meeee., (8888) 88, 88888.
[639] Mee'eeeee, M. M.; Mee'eeeeeeeee, M. M., Me. Meeeee. Meee., (8888) 88, 888; Meee. Meeee., (8888) 88, 88888.
[640] Meeeeee, M. M.; Meeee, M. M.; Meeeee, M. M., (Meeeeeee Meeeeeee Me.), MM 8888888, (8888); Meee. Meeee., (8888) 88, 88888.
[641] Meeee, M.; Meeee, M.; Meeeee, M., Meeeeee. Meeee. Meee. Meeeee., (8888) 88, 8888.
[642] Meeeeeeeee, M. M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 888.
[643] Meee-Meee, M., Meeeeeeeeee Meee., (8888), 88.
[644] Meeeeeeeee, M., (Meee. Mee Meeeeeee Me.), MM 8888888; Meee. Meeee., (8888) 88, 8888.
[645] Meeeee, M. M.; Meeeeeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 888.
[646] Meeeee, M. M.; MeMeeee, M. M., Mee. Meeee., (8888) 88, 88.
[647] Meeeeeee, M.; Meeeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888.
[648] Meeee, M.; Meeeee, M.; Meeeeee, M., (Meee Meeeee Meeeeeeeee Mee.), MM 8888, (8888); Meee. Meeee., (8888) 88, 8888.
[649] Meeeeeee, M., Meee. Mee. Meee. Me., (8888), 888.

Meeeeee Meeeeeeeeee

  • 8.Meeeee-Meee, (8888) 8/8, 8888.
  • 8.Meeeee-Meee, (8888) M 8e, 888.

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