Hydrochloric Acid → HCID 12988689, compound

HRID 1593818Notes

Reaction equation

HRID 1593818 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8](I)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])O.[Na+].[CH2:17]([OH:20])[CH:18]=[CH2:19].Cl>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.Cl[Pd]Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:19][CH2:18][CH:17]=[O:20])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7858Allyl AlcoholHCID 516892Sodium BicarbonateHCID 5196382-Chloro-5-iodobenzoic acid

Product 1

HCID 12988689HCID 12988689, compound

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 70681Tetrabutylammonium ChlorideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-5-iodobenzoic acid (5.0 g), tetrabutylammonium chloride (5.0 g), sodium hydrogencarbonate (5.3 g) and allyl alcohol (1.6 ml) were combined in N,N-dimethylformamide (50 ml) and PdCl2 (0.6 g) was added under nitrogen. After 24 h ethyl acetate and 2 M hydrochloric acid were added to the crude reaction mixture and the precipitated Pd filtered off. The organic phase was separated and washed thrice with 2 M hydrochloric acid then once with brine and dried over magnesium sulfate, filtered and evaporate. Purification by chromatography on silica (eluting ethyl acetate:acetic acid/19:1) gave the subtitled product as an oil (2.77 g).

Workup

  1. customreaction mixture
  2. filtrationthe precipitated Pd filtered off
  3. customThe organic phase was separated
  4. washwashed thrice with 2 M hydrochloric acid
  5. dry with materialonce with brine and dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporate
  8. customPurification by chromatography on silica (eluting ethyl acetate:acetic acid/19:1)

Sources & evidence

ORD record
ord-969f7ab448274f859913eb5f164461cf
Source dataset
uspto-grants-2007_11
Patent number
US07297818B2

Reaction notes

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