Hydrochloric Acid → HCID 12988689, compound

HRID 1816050Notes

Reaction equation

HRID 1816050 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 2M hydrochloric acid were added to the crude reaction mixture and the precipitated Pd filtered off. The organic phase was separated and washed thrice with 2M 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 2M 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-9dd8ad4c0c2b47b497648c8bc364b2cc
Source dataset
uspto-grants-2005_04
Patent number
US06881754B2

Reaction notes

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