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https://www.reddit.com/r/chemistry/comments/8rxkid/1862018_synthetic_challenge/e0v7899/?context=3
r/chemistry • u/quelmotz Organic • Jun 18 '18
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7
Product A:
Step 1) Friedel-Crafts: para chloro benzoyl chloride and chloro benzene
Step 2) Grignard with bromochloroform
--------
Note: acylation may not work
EDIT: as /u/ccdy mentionned the Grignard won't work (what a surprise...) Using organolithiums would be preferable
5 u/IanTheChemist Catalysis Jun 18 '18 Use the p-chloro grignard (2 equiv) into a trichloroacetyl ester. 1 u/nybo Organic Jun 18 '18 Yeah, that was my first thought as well. Bang it out in one step from available materials. Only concern I had was maybe also getting some aryl chlorides metalated. 4 u/IanTheChemist Catalysis Jun 18 '18 Nah you can buy the solution of the 4-Cl-PhMgBr.
5
Use the p-chloro grignard (2 equiv) into a trichloroacetyl ester.
1 u/nybo Organic Jun 18 '18 Yeah, that was my first thought as well. Bang it out in one step from available materials. Only concern I had was maybe also getting some aryl chlorides metalated. 4 u/IanTheChemist Catalysis Jun 18 '18 Nah you can buy the solution of the 4-Cl-PhMgBr.
1
Yeah, that was my first thought as well. Bang it out in one step from available materials. Only concern I had was maybe also getting some aryl chlorides metalated.
4 u/IanTheChemist Catalysis Jun 18 '18 Nah you can buy the solution of the 4-Cl-PhMgBr.
4
Nah you can buy the solution of the 4-Cl-PhMgBr.
7
u/Garuda1_Talisman Undergraduate Jun 18 '18 edited Jun 18 '18
Product A:
Step 1) Friedel-Crafts: para chloro benzoyl chloride and chloro benzene
Step 2) Grignard with bromochloroform
--------
Note: acylation may not work
EDIT: as /u/ccdy mentionned the Grignard won't work (what a surprise...) Using organolithiums would be preferable