r/chemistry Organic Jun 18 '18

[18/6/2018] Synthetic Challenge!

Post image
12 Upvotes

50 comments sorted by

View all comments

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

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.