Hydrochloric Acid → 2,6-difluoro-N-[(Z)-prop-1-enyl]benzamide

HRID 1479158Notes

Reaction equation

HRID 1479158 reaction equation
[CH3:1][Mg+].[Br-].[F:4][C:5]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:6]=1[C:7]([NH:9]/[CH:10]=[CH:11]\I)=[O:8].Cl>[Br-].[Zn+2].[Br-].C(OCC)C.C1COCC1.CN(C=O)C>[F:4][C:5]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:6]=1[C:7]([NH:9]/[CH:10]=[CH:11]\[CH3:1])=[O:8]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 897610472,6-difluoro-N-[(Z)-2-iodovinyl]benzamideHCID 178418689HCID 178418689, compound

Product 1

HCID 897607922,6-difluoro-N-[(Z)-prop-1-enyl]benzamideYield 86%

Reagents, catalysts & solvents 4

HCID 10421208Zinc bromideCatalystHCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Zinc bromide (1.68 g, 7.48 mmol) was added in portions to a solution of MeMgBr in diethyl ether (3M, 2.4 ml, 7.23 mmol).After stirring at room temperature there was a thick prepicipitate. Some DMF and THF was added to improve solubility and aid stirring. 2,6-difluoro-N—[(Z)-2-iodovinyl]benzamide (746 mg, 2.41 mmol) was added and then dichloro-bisacetonitrile palladium (12.5 mg, 0.048 mmol) was added, and the mixture stirred overnight at RT and then shaken between diethyl ether and HCl (1 M), dried with MgSO4, evaporated and chromatographed with EtOAc/cyclohexane to yield pure 2,6-difluoro-N—[(Z)-prop-1-enyl]benzamide (406 mg, 86%) m.p. 71-74° C.

Workup

  1. stirringstirring
  2. stirringthe mixture stirred overnight at RT
  3. dry with materialdried with MgSO4
  4. customevaporated
  5. customchromatographed with EtOAc/cyclohexane

Sources & evidence

ORD record
ord-14ed8373ac744093829069774fbaeedc
Source dataset
uspto-grants-2016_08
Patent number
US09408392B2

Reaction notes

Loading…