Hydrochloric Acid → HCID 66915550, compound

HRID 449126Notes

Reaction equation

HRID 449126 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[Cl-].[Cl-].[Cl-].[Al+3].Cl>C1C=CC=CC=1.CN(C=O)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([C:2]2[CH:11]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:14])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 2825914-Bromo-1-naphthoic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 66915550HCID 66915550, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

an oven dried flask was added 4-bromo-naphthalene-1-carboxylic acid In (1.36 g, 0.0054 mol), thionyl chloride (0.77 mL, 0.010 mol) and a drop of DMF and the reaction was refluxed for 2 h. The thionyl chloride was then distilled off and benzene (20 mL) and aluminum trichloride (0.676 g, 0.0051 mol) was added to the reaction mixture and the reaction was stirred at room temp for 1 h. The crude reaction mixture was poured onto ice and conc HCl (15 mL). The organic layer was separated and the aqueous layer extracted with EtOAc. The combined organic phases were washed with 5% aq NaOH solution, water and dried (Na2SO4). The organic phase was concentrated in vacuo to give a residue which was purified by silica gel chromatography, eluting with 2% EtOAc in hexane.

Workup

  1. customan oven dried flask
  2. distillationThe thionyl chloride was then distilled off
  3. customThe crude reaction mixture
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with EtOAc
  6. washThe combined organic phases were washed with 5% aq NaOH solution, water
  7. dry with materialdried (Na2SO4)
  8. concentrationThe organic phase was concentrated in vacuo
  9. customto give a residue which
  10. customwas purified by silica gel chromatography
  11. washeluting with 2% EtOAc in hexane

Sources & evidence

ORD record
ord-e1db32bdf88f42e7835cd9b080db10c3
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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