Water → HCID 86722252, compound

HRID 869407Notes

Reaction equation

HRID 869407 reaction equation
[C:1]([C:4]1[O:5][C:6]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([Br:15])[C:7]=2[C:8]=1[NH2:9])(=[O:3])[CH3:2].[F-].[Cs+].[CH3:18]I.O>C1COCC1>[C:1]([C:4]1[O:5][C:6]2[CH:13]=[CH:12][C:11]([O:14][CH3:18])=[C:10]([Br:15])[C:7]=2[C:8]=1[NH2:9])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 25953Cesium fluorideHCID 86722251HCID 86722251, compound

Product 1

HCID 86722252HCID 86722252, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 12F (5.6 g, 0.020 mol) and CsF (9.5 g, 0.0625 mol) in THF (20 mL) was added MeI (2.9 g) dropwise at room temperature. The reaction mixture was stirred at room temperature for 1 hour, then added dropwise into water. The solids were precipitated out dissolved in ethyl acetate and purified by column chromatography on silica gel to give 12G (2.4 g, 40.7% yield).

Workup

  1. customThe solids were precipitated
  2. dissolutionout dissolved in ethyl acetate
  3. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f436c9b2248b4f75b8fb50f49763a398
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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