Organic and Medicinal Chemistry Letters

Table 1 Optimization of the reaction conditions following Figure 1

From: Facile synthesis of symmetrical bis(benzhydryl)ethers using p-toluenesulfonyl chloride under solvent-free conditions

Entry	p-TsCl (mol%)	Solvent	Temperature (°C)	Time (min)	Yield (%) ^a
1	0	-	110	120	No reaction
2	10	-	90	25	82
3	10	-	110	15	87
4	5	-	90	35	80
5	5	-	110	15	86
6	5	-	Rt	240	Trace
7	3	-	110	75	28
8	10	CH₂Cl₂	Rt	1,050	19
9	5	CH₂Cl₂	Rt	1,050	Trace
10	10	THF	Rt	600	Trace
11	10	CH₃CN	Rt	720	17
12	10	CH₂Cl₂	Reflux	300	36
13	50	-	110	5	43 (tosylate: 47)
14	100	-	110	5	7 (tosylate: 91)

^aIsolated yield; RT, room temperature; p-TsCl, p-toluenesulfonyl chloride; Tosylate, benzhydryl p-toluenesulfonate.

Back to article page