Iodine → HCID 131721611, compound

HRID 850233Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([O:8][SiH2:9][C:10]([CH3:15])([CH3:14])[CH2:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[CH:16]=[C:17](Br)Br.C([Li])CCC.[I:25]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([O:8][SiH2:9][C:10]([CH3:15])([CH3:14])[CH2:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[C:16]#[C:17][I:25]

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of 26 mmol of 1-(2-fluoro-4-dimethylbutylsilyloxyphenyl)-2,2-dibromoethylene in 50 ml of tetrahydrofurane were added dropwise 134 ml of n-butyl lithium (1.6M), while stirring at -70° C. After completion of the addition, the reaction solution was stirred for 3 hours, 10 ml tetrahydrofuran solution of 30 mmol of iodine were added dropwise and the solution was gradually elevated to room temperature. Afer completion of the agitation, the solution was poured into a sodium thiosulfate solution and extracted with heptane. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a brown solid. Purification of the solid by a silica gel column chromatography gave 25 mmol of 1-(2-fluoro-4-dimethylbutylsilyloxyphenyl)-2-iodoethyne as a yellow solid.

Workup

additionAfter completion of the addition
stirringthe reaction solution was stirred for 3 hours
customwas gradually elevated to room temperature
extractionextracted with heptane
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customto afford a brown solid
customPurification of the solid by a silica gel column chromatography

Sources & evidence

ORD record: ord-f539b3fff84c4828b98e0393069165dc
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06017467

Reaction notes

Loading…