Table 2. Optimization of Reaction Conditions and Purification of 6.

entry	alcohol (mmol)	equiv NaClOa	equiv KBr	equiv nBu4NBr	equiv TEMPO	time (min)	bisulfite extractionb	conversion (%)	yield (%)c
1	0.42	1.5	0.1	0.05	0.05	120		69	ND
2	0.42	1.8	0.1	0.05	0.05	15		100	ND
3	4.22	1.8	0.1	0.05	0.05	15	2 h r.t.	100	31
4	4.22	1.7	0.1		0.05	60	2 h r.t.	100	59
5	4.22	1.7	0.1		0.01	30	2 h r.t.	100	71
6	37.00	1.7	0.1		0.01	30	2 h r.t.	100	60
7	37.00	1.6	0.1		0.01	15	2 h r.t.	100	66
8	73.00	1.6	0.1		0.01	15	2 h r.t.	100	59
9	73.00	1.6	0.1		0.01	15	16 h r.t.	100	71

^aNaClO concentration (11–15%).

^bStirred for 1 h at 0 °C before filtration.

^cIsolated yield.