Dolbier HW Solutions 551

Dolbier HW Solutions 551 - CH 3 CH 2 CH 2 CH 3 NH 2 Br CH 2...

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( g ) The orientation of substituents in the target molecule can be achieved by using an amino group to control the regiochemistry of bromination, then removing it by reductive deamination. The amino group is introduced in the standard fashion by nitration of an arene followed by reduction. This analysis leads to the synthesis shown. HNO 3 H 2 , Ni ethanol 1. NaNO 2 , H 1 , H 2 O 2. H 3 PO 2 CH 3 CH 2 CH 2 CH 3 m -Diethylbenzene CH 3 CH 2 CH 2 CH 3 NO 2 2,4-Diethyl-1-nitrobenzene (75 80%) 1-Bromo-3,5- diethylbenzene (70%) CH 3 CH 2 CH 2 CH 3 Br Br 2 CH 2 CH 3 CH 3 CH 2 NH 2 2,4-Diethylaniline (80 90%) 2-Bromo-4,6- diethylaniline (40%)
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Unformatted text preview: CH 3 CH 2 CH 2 CH 3 NH 2 Br CH 2 CH 3 CH 3 CH 2 NH 2 CH 3 CH 2 CH 2 CH 3 Br CH 3 CH 2 CH 2 CH 3 NH 2 Br hydrolysis to remove acetyl group Cl 2 C(CH 3 ) 3 NHCCH 3 O 4-tert-Butyl-2-chloroacetanilide Cl 1. NaNO 2 , H 1 2. H 3 PO 2 NH 2 Cl C(CH 3 ) 3 4-tert-Butyl-2-chloroaniline C(CH 3 ) 3 Cl m-tert-Butyl-chlorobenzene C(CH 3 ) 3 NO 2 p-tert-Butyl-nitrobenzene C(CH 3 ) 3 NH 2 p-tert-Butyl-aniline C(CH 3 ) 3 NHCCH 3 O p-tert-Butyl-acetanilide H 2 , Ni acetic anhydride AMINES 645...
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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