Carbon Dioxide → HCID 86667933, compound

HRID 2179841Notes

Reaction equation

[Br-].[Li+].[F:3][C:4]([F:16])([C:9]1([C:12]([F:15])([F:14])[F:13])[CH2:11][O:10]1)[C:5]([F:8])([F:7])[F:6].[C:17](=[O:19])=[O:18]>CN1CCCC1=O>[C:17]1(=[O:18])[O:10][CH2:11][C:9]([C:12]([F:15])([F:14])[F:13])([C:4]([F:16])([F:3])[C:5]([F:8])([F:7])[F:6])[O:19]1

Participants

Conditions

Temperature: 100 °C

Procedure

73 mL N-methylpyrrolidone (NMP) was introduced into a 500-mL autoclave; 1.5 g (17 mmol) lithium bromide and 132 g (575 mmol) 2-pentafluoroethyl-2-trifluoromethyloxirane were charged; and the interior of the system was replaced with CO2 5 times. The reaction solution was heated to 100° C. and pressurization with CO2 at 0.8 MPa was performed until the starting epoxide had disappeared. After the reaction was finished, the reaction solution was returned to room temperature; quenching was performed with 300 mL 1 N aqueous hydrochloric acid; separation was carried out and the organic layer was dried over magnesium sulfate; and suction filtration was performed. The filtrate was subjected to rectification under reduced pressure using a 10-stage Oldershaw column to obtain 113 g (isolated yield=72%, purity=99.7%) 1-trifluoromethyl-1-pentafluoroethylethylene carbonate (=4-pentafluoroethyl-4-trifluoromethyl-1,3-dioxolan-2-one). Molecular Sieve 3A (Wako Pure Chemical Industries, Ltd.) was then introduced and the water content was reduced to 30 ppm.

Workup

customwas returned to room temperature
customquenching
customseparation
dry with materialthe organic layer was dried over magnesium sulfate
filtrationand suction filtration

Sources & evidence

ORD record: ord-2785a181b0eb4bca9ca469e2dc1a3dfd
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09070951B2

Reaction notes

Loading…