Cesium fluoride → HCID 68289659, compound

HRID 878770Notes

Reaction equation

HRID 878770 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15].[F-].[Cs+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:15]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1)[CH:14]=[CH2:13]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 90628AllyltributylstannaneHCID 113453114-Bromo-2-fluoro-benzoic acid methyl ester

Product 1

HCID 68289659HCID 68289659, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-bromo-2-fluorobenzoate (424 mg, 1.82 mmol), allyl tributyl tin (0.846 mL, 2.73 mmol), tetrakis(triphenylphosphine)palladium (0) (105 mg, 0.091 mmol) and cesium fluoride (415 mg, 2.73 mmol) were heated to reflux in 1,4-dioxane (10 mL) for 7 hours under argon atmosphere. The mixture was cooled to room temperature, and then filtered through diatomaceous earth by ethyl acetate and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2%→10%) to give methyl 4-allyl-2-fluorobenzoate (333 mg, 94%) as a pale yellow viscous material.

Workup

  1. filtrationfiltered through diatomaceous earth by ethyl acetate
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2%→10%)

Sources & evidence

ORD record
ord-1fe75cae6f2d4a7797eafe28285fddd2
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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