1,2-Difluoro-1,2-diphenylethane → 1,1-Difluoro-2,2-diphenylethane

HRID 2201600Notes

Reaction equation

HRID 2201600 reaction equation
CC1C=C(C(C)(C)C)C=C(C)C=1S(F)(F)[F:14].[CH:17]1[CH:22]=[CH:21][C:20]([C@@H:23](O)[C@@H:24](O)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=C[CH:18]=1.FC(C1C=CC=CC=1)[CH:35]([F:42])C1C=CC=CC=1>C(Cl)Cl>[F:14][CH:35]([F:42])[CH:24]([C:23]1[CH:18]=[CH:17][CH:22]=[CH:21][CH:20]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 5730531,2-Difluoro-1,2-diphenylethaneHCID 853018Hydrobenzoin, meso-HCID 441847004-tert-Butyl-2,6-dimethylphenylsulfur trifluoride

Product 1

HCID 138160411,1-Difluoro-2,2-diphenylethaneYield 0.03%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 15 mL fluoropolymer flask, 2,6-dimethyl-4-tert-butylphenylsulfur trifluoride (0.625 g, 2.5 mmol) was dissolved in 5 mL of anhydrous CH2Cl2. A solution of meso-1,2-diphenyl-1,2-ethanediol (0.214 g, 1.0 mmol) in 5 mL of anhydrous CH2Cl2 was added to the above stirred solution at room temperature. After 3 hours, C12H26F was added as standard, the 19F NMR analysis showed that 1,2-difluoro-1,2-diphenylethane (PhCHFCHFPh) was produced in 97% yield and a trace (˜0.03%) of 1,1-difluoro-2,2-diphenylethane (Ph2CHCF2H) was formed. Products were characterized by comparing to the spectroscopic data in literature (see Journal of Fluorine Chem. Vol. 125, pp 1869-1872 (2004)).

Workup

  1. customwas produced in 97% yield

Sources & evidence

ORD record
ord-afa1bba5f3714ff2906433b8c39a8b5f
Source dataset
uspto-grants-2016_06
Patent number
US09365471B2

Reaction notes

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