HCID 118656363, compound → HCID 87445672, compound
Reaction equation
FS(C1C=CC([O:11][CH:12]([C:17]([F:20])([F:19])[F:18])[C:13]([F:16])([F:15])[F:14])=CC=1)(=O)=O.[F:21][C:22]([F:40])([F:39])[CH:23]([C:35]([F:38])([F:37])[F:36])[O:24]C1C=CC(S([O-])(=O)=O)=CC=1>>[F:14][C:13]([F:16])([F:15])[CH:12]([OH:11])[C:17]([F:20])([F:19])[F:18].[CH:23]([OH:24])([C:35]([F:38])([F:37])[F:36])[C:22]([F:40])([F:39])[F:21]Participants
Procedure
Diazonium salt 1 (106.8 mg, 0.3359 mmol) was dissolved in HFIP (7.16 g) and the mixture was heated at 60° C. for 4 h. After cooling, Na2CO3 was added and the mixture was filtered. Most of the solvent was evaporated to give a pale-yellow oil, which was purified by SiO2 column chromatography with hexane/CH2Cl2 (9:1) to afford 1-(pentafluorosulfanyl)-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]benzene (colorless oil; 2.0 mg, 1.6%), 1-fluoro-4-(fluorosulfonyl)benzene (Ferm & VanderWerf, J. Am. Chem. Soc. 1950, 72, 4809-4810) (colorless oil; 7.7 mg, 13%), and 2,2,2-trifluoro-1-(trifluoromethyl)-ethyl 4-fluorophenylsulfonate (Popov, et al., Ukrainskii Khim. Zh. 1991, 57, 843-849) (colorless oil; 15.7 mg, 14.3%). Elution with hexane/CH2Cl2 (8:2) gave 1-(fluorosulfonyl)-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]benzene (colorless oil, 6.6 mg, 6.0%), a 2:1 mixture of 1-(fluorosulfonyl)-4-[2,2,2-trifluoro-1-(trifluoromethyl) ethoxy]benzene and 2,2,2-trifluoro-1-(trifluoromethyl)ethyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]phenylsulfonate (colorless oil, 27.2 mg, 19.1%), and 4-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]phenylsulfonate (colorless oil, 3.8 mg, 2.4%).
Sources & evidence
- ORD record
- ord-af424d38ddff42bc8a3e46464aab4ad9
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238660B1
Reaction notes
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