Method of producing pentafluorosulfanyl aromatic compound

Patent metadata

Field	Value
Publication number	US-11014887-B2
Application number	US-201816489275-A
Country	US
Kind code	B2
Filing date	Feb 26, 2018
Priority date	Feb 28, 2017
Publication date	May 25, 2021
Grant date	May 25, 2021

Abstract

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.

First claim

The invention claimed is:

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).

Assignees

• Ube Industries

Inventors

• Shibata Norio
• Saito Norimichi

Classifications

• C07C381/00 Primary

  Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00 · CPC title

• C07D213/71 Primary

  to which a second hetero atom is attached · CPC title

• C07D239/38

  One sulfur atom · CPC title

• C07D277/76

  Sulfur atoms attached to a second hetero atom · CPC title