Page 1045 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Scheme 11.4. Friedel-Crafts Acylation Reactions 1021

A. Intermolecular reactions SECTION 11.1
Br
1 a Br Electrophilic Aromatic
Substitution
+ (CH CO) O AlCl 3
2
3
69–79%
O CCH 3
2 b
CH O
CH 3 3
O
CCH 3
+ CH CCl AlCl 3
3
50–55%
CH(CH ) CH(CH )
3 2
3 2
3 c O
O
CCH H
AlCl 3 CHCO 2
+ O
80–85%
O
O O
4 d
NHCCH 3 NHCCH 3
O
AlCl 3
+ ClCCH 2 Cl
80–85%
O CCH 2 Cl
5 e
) NCH CH O
OCH CH N(CH ) (CH 3 2 2 2 Ph
2
2
3 2
PhCHC H (CF CO) O
2 5
3
2
+ CO H 85% H PO 4 C H
2 5
3
2
O
96%
6 f O
Bi(O SCF ) , O
3 3
3
F + PhCCl 10 mol % F
Ph
86%
B. Intramolecular friedel–crafts acylations
7 g (CH ) CO H
2
2 3
PPA 75–86%
O
8 h O
) CCl
(CH 2 3 AlCl 3
O 74–91%
9 i O O
+ O AlCl 3
91–96%
(Continued)