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35.2.3.3.3.1 Substitution of Oxygen Functionalities

DOI: 10.1055/sos-SD-135-00227

Braun, M.Science of Synthesis Knowledge Updates, (20171461.

Most of the procedures that permit the conversion of nonactivated aliphatic alcohols into the corresponding bromoalkanes, as described in Section 35.2.1.5, have been applied to benzylic alcohols. These procedures include the use of 7,7-dichlorocyclohepta-1,3,5-triene (1) and lithium bromide (Scheme 1, entries 1 and 2),[‌1‌] oxalyl chloride, lithium bromide, and triphenylphosphine oxide (entries 3 and 4),[‌2‌] ethyl 2,2-dibromo-3-oxobutanoate (2) and triphenylphosphine (entries 5–9),[‌3‌] 1,1,1,3,3,3-hexabromopropan-2-one (3) and triphenylphosphine (entries 10–24),[‌4‌] 2,2-dibromo-1,3-dicyclohexylimidazolidine-4,5-dione (4; entries 25–28),[‌5‌] 1-butyl-3-methylimidazolium hydrogen sulfate (5) and sodium bromide (entries 29–34),[‌6‌] 3-methyl-1-pentylimidazolium bromide (6) and tert-butyl bromide (entries 35–38),[‌7‌] N-bromosaccharin (7) and triphenylphosphine (entries 39–43),[‌8‌] and bromine and imidazolium hexafluorophosphate derivative 8 (entries 44–48);[‌9‌] the latter method is also applicable to silyl- and tetrahydropyranyl-protected benzylic alcohols.

Meeeee 8 Meeeeeeeee ee Meeeeeee Meeeeeee eeee Meeeeeee Meeeeeee[‌8‌‌8‌]

Meeeeeeeeee 8

Meeee Me8 M8 Meeeeeeeee Meeeee (%) Mee
8 Me M 8,e MeMe (8.8 eeeee), MM8Me8, 88 °M 88 [‌8‌]
8 8-M8MM8M8 M 8,e MeMe (8.8 eeeee), MM8Me8, 88 °M 88 [‌8‌]
8 Me M MeMe, (MMMe)8, Me8MM (eee.), MMMe8, 88 °M 88 (88)e [‌8‌]
8 Me Me MeMe, (MMMe)8, Me8MM (eee.), MMMe8, 88 °M 88 [‌8‌]
8 8,8-Me8M8M8 M 8, Me8M, 8,8-eeeeeeeeeeeeee, 88 °M 88 [‌8‌]
8 Me MM8MM=MM8 8, Me8M, 8,8-eeeeeeeeeeeeee, 88 °M 88 [‌8‌]
8 8,8-Me8M8M8 MM8MM=MM8 8, Me8M, 8,8-eeeeeeeeeeeeee, 88 °M 88 [‌8‌]
8 Me eeeeeeeeeee 8, Me8M, 8,8-eeeeeeeeeeeeee, 88 °M 88e [‌8‌]
8 8-MM8M8 eeeeeeeeeee 8, Me8M, 8,8-eeeeeeeeeeeeee, 88 °M 88e [‌8‌]
88 Me M 8, Me8M, MeMM, 88 °M, eeeeeeeee 888e [‌8‌]
88 8-Mee M 8, Me8M, MeMM, 88 °M 888e [‌8‌]
88 8-MeMM8M8 M 8, Me8M, MeMM, 88 °M 888e [‌8‌]
88 8-MeM8M8 M 8, Me8M, MeMM, 88 °M 888e [‌8‌]
88 8-Mee M 8, Me8M, MeMM, 88 °M 888e [‌8‌]
88 8-MeMM8M8 M 8, Me8M, MeMM, 88 °M 888e [‌8‌]
88 8-MeM8M8 M 8, Me8M, MeMM, 88 °M 888e [‌8‌]
88 8-M8MM8M8 M 8, Me8M, MeMM, 88 °M 888e [‌8‌]
88 8-M8MM8M8 M 8, Me8M, MeMM, 88 °M 88e [‌8‌]
88 8-eeeeeeee M 8, Me8M, MeMM, 88 °M 888e [‌8‌]
88 8-eeeeeeee Me 8, Me8M, MeMM, 88 °M 888e [‌8‌]
88 8-eeeee M 8, Me8M, MeMM, 88 °M 88e [‌8‌]
88 8-eeeeeee M 8, Me8M, MeMM, 88 °M 888e [‌8‌]
88 8-eeeeeee M 8, Me8M, MeMM, 88 °M 888e [‌8‌]
88 M 8, Me8M, MeMM, 88 °M 88e [‌8‌]
88 Me M 8, MM8Me8, 88 °M 88 [‌8‌]
88 Me Me 8, MM8Me8, 88 °M 88e [‌8‌]
88 8-M8MM8M8 M 8, MM8Me8, 88 °M 88 [‌8‌]
88 8-eeeeeee M 8, MM8Me8, 88 °M 88 [‌8‌]
88 Me M 8, MeMe, eeeeeeeee eeeeeeeeeee 88 [‌8‌]
88 8-M8MM8M8 M 8, MeMe, eeeeeeeee eeeeeeeeeee 88 [‌8‌]
88 8-MeMM8M8 M 8, MeMe, eeeeeeeee eeeeeeeeeee 88 [‌8‌]
88 8-MeM8M8 M 8, MeMe, eeeeeeeee eeeeeeeeeee 88 [‌8‌]
88 8,8,8-(MeM)8M8M8 M 8, MeMe, eeeeeeeee eeeeeeeeeee 88 [‌8‌]
88 M 8, MeMe, eeeeeeeee eeeeeeeeeee 88 [‌8‌]
88 Me M 8, e-MeMe, eeeeeeeeee 88 [‌8‌]
88 8-MeMM8M8 M 8, e-MeMe, eeeeeeeeee 88 [‌8‌]
88 8-MeM8M8 M 8, e-MeMe, eeeeeeeeee 88 [‌8‌]
88 M 8, e-MeMe, eeeeeeeeee 88 [‌8‌]
88 Me M 8, Me8M, MM8Me8, 88 °M 88 [‌8‌]
88 Me Me 8, Me8M, MM8Me8, 88 °M 88 [‌8‌]
88 8-MeMM8M8 M 8, Me8M, MM8Me8, 88 °M 88 [‌8‌]
88 8-MeM8M8 M 8, Me8M, MM8Me8, 88 °M 88 [‌8‌]
88 8-M8MM8M8 M 8, Me8M, MM8Me8, 88 °M 88 [‌8‌]
88 Me M 8, Me8, 88 °M 88 [‌8‌]
88 Me Me 8, Me8, 88 °M 88 [‌8‌]
88 Me Me 8, Me8, 88 °M 88 [‌8‌]
88 8-MeMM8M8 M 8, Me8, 88 °M 88 [‌8‌]
88 8-M8MM8M8 M 8, Me8, 88 °M 88 [‌8‌]

e Meeeeeee eeeee, eeeeee eeeeeeeee eeeeee.

e 8,8-Meeeeeeeeeeeeeeeee-8,8,8-eeeeee eee eeeeeeeee ee eeee eeee eeeeeee eee eeeeee eeeeeeee.

e Meeee ee eeeeeeeeeee ee eeeee eeeeeeeeee ee 8M MMM eeeeeeeeeeee eeeee 8,8,8,8-eeeeeeeeeeeeeeeee ee eeeeeeee eeeeeeee.

e (M)-8-Meeee-8-eeeeeeeee-8-eee eee eeeeeeee.

e (M)-8-Meeee-8-(8-eeeeeeeeeeee)eee-8-eee eee eeeeeeee.

e Meeee eeeeeeeeee ee 8M MMM eeeeeeeeeeee.

e 88% ee eee eeeeeeeee, 8% ee eee eeeeeee.

Meeeeeeeeeee Meeeeeeee

Meeeee Meeeeee (88, Me8 = Me; M8= M); Meeeeee Meeeeeeee Meeee eeee-Meeee Meeeeee eee 8-Meeeee-8-eeeeeeeeeeeeeeeee Meeeeee:[‌8‌]

M eeeeeee ee eeeeee eeeeeee (8, Me8 = Me; M8= M; 888 ee, 8 eeee) eee e-MeMe (888 ee, 8 eeee) ee eee eeeee eeeeee 8-eeeeee-8-eeeeeeeeeeeeeeeee eeeeeee (8; 8.8 e) eee eeeeeeeee ee ee eeeeeeeeee eeee eee 8.8 e. Meeeee eeeeeeeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eeee eee eeeeeee ee e eeeeeeeee eeeeee; eeeee: 888 ee (88%). Mee eeeeeee eee eeeeee eeeeeeeeee ee eeeeeeeeee ee eee eeeeeee (8M eee 88M MMM) eeee eeeee ee ee eeeeeeeee eeeeee.

Meeeee Meeeeee (88, Me8 = Me; M8= M); Meeeeee Meeeeeeee Meeee M-Meeeeeeeeeeeee eee Meeeeeeeeeeeeeeeee:[‌8‌]

Meeeee eeeeeee (8, Me8 = Me; M8= M; 8.88 e, 8 eeee) eee eeeee ee 88 °M ee e eeeeeee ee M-eeeeeeeeeeeeee (8; 8.888 e, 8 eeee) eee Me8M (8.888 e, 8 eeee) ee eeeee MM8Me8 (88 eM). Mee eeeeeeee ee eee eeeeeeee eee eeeeeeeee ee MMM. Mee eeeeeeee eee eeeeeeee eeeeeeeeeee. Mee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8); eeeee: 8.88 e (88%).

References


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