Method of producing pentafluorosulfanyl aromatic compound
View Patent ↗A method of producing a pentafluorosulfanyl aromatic compound is provided. A method of producing a pentafluorosulfanyl aromatic compound represented by general formula (3): Ar—(SF 5 ) k (3) where Ar is a substituted or an unsubstituted aryl group or heteroaryl group, and k is an integer of 1 to 3; the method includes reacting IF 5 with a halotetrafluorosulfanyl aromatic compound represented by general formula (2): Ar—(SF 4 Hal) k (2) where Ar and k are defined as above; and Hal is a Cl group, a Br group, or an I group.
1. A method of producing a pentafluorosulfanyl aromatic compound represented by general formula (3):
Ar—(SF 5 ) k (3)
wherein Ar is a substituted or an unsubstituted aryl group or heteroaryl group and
k is an integer of 1 to 3;
the method comprising reacting IF 5 with a halotetrafluorosulfanyl aromatic compound represented by general formula (2):
Ar—(SF 4 Hal) k (2)
wherein Ar and k are defined as above; and
Hal is a Cl group, a Br group, or an I group.
2. The method according to claim 1 , wherein the aryl group or heteroaryl group has a substituent selected from the group consisting of a halogen group, an electron-withdrawing group excluding halogen groups, and an electron-donating group excluding halogen groups.
3. The method according to claim 1 , wherein the halotetrafluorosulfanyl aromatic compound and the pentafluorosulfanyl aromatic compound are represented by general formulae (2′) and (3′), respectively:
wherein: Hal is a Cl group, a Br group, or an I group;
X is C or N;
Y is C or N;
R is each independently a halogen group, an electron-withdrawing group excluding halogen groups, or an electron-donating group excluding halogen groups;
k is an integer of 1 to 3;
m is an integer represented by 0 to (5−k−n); and
n is the number of N.
4. The method according to claim 1 , wherein the substituent is an electron-withdrawing group excluding halogen groups, and the reaction is performed at 50° C. or higher.
5. The method according to claim 1 , wherein the substituent is an electron-withdrawing group excluding halogen groups, and 1 equivalent or more of IF 5 is used for the SF 4 Hal group, that is the halotetrafluorosulfanyl aromatic compound represented by general formula (2).
6. The method according to claim 3 , wherein:
at least one of X and Y is N; and
at least one of R is an electron-withdrawing group excluding halogen groups, the electron-withdrawing group being present at the 3-position of the ring.
7. The method according to claim 1 , wherein the halotetrafluorosulfanyl aromatic compound and the pentafluorosulfanyl aromatic compound are represented by general formulae (2″) and (3″), respectively:
wherein Hal is a Cl group, a Br group, or an I group;
Z is N or S;
p is an integer of 0 to 2;
R′ is each independently a halogen group, an electron-withdrawing group excluding halogen groups, or an electron-donating group excluding halogen groups; and
q is an integer represented by 0 to (4−p).