2,3-Dibromopropene → HCID 22117505, compound

HRID 1275791Notes

Reaction equation

[C:1]1([CH:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[Br:25][C:26]([CH2:28]Br)=[CH2:27]>C1COCC1>[C:1]1([C:7]2([CH2:28][C:26]([Br:25])=[CH2:27])[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 9-phenylfluorene in anhydrous THF is cooled to -78° C. under a nitrogen atmosphere. A solution of nBuLi in hexanes (1 eq) is added dropwise via syringe. After stirring at -78° C. for 10 min a solution of 2,3-dibromopropene (1.2eq) in THF is added dropwise via syringe. The solution is stirred at -78° C. for 1 h and then allowed to warm to room temperature. The reaction mixture is quenched by the addition of sat. aq NH4Cl. The resulting mixture is extracted with ether. The organic layer is washed with H2O and then brine, dried (Na2SO4), and concentrated in vacuo. The concentrate is purified by flash chromatography on silica gel eluting with hexanes-ethyl acetate to afford the title compound.

Workup

additionis added dropwise via syringe
temperatureto warm to room temperature
customThe reaction mixture is quenched by the addition of sat. aq NH4Cl
extractionThe resulting mixture is extracted with ether
washThe organic layer is washed with H2O
dry with materialbrine, dried (Na2SO4)
concentrationconcentrated in vacuo
customThe concentrate is purified by flash chromatography on silica gel eluting with hexanes-ethyl acetate

Sources & evidence

ORD record: ord-7f5fb725b9df4222a9a752764a3b458a
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06162824

Reaction notes

Loading…