Boron tribromide → HCID 135574102, compound

HRID 1955344Notes

Reaction equation

HRID 1955344 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH:11]=[CH:12][CH:13]=[N:14]3)=[CH:5][CH:4]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:14]1[C:15]2[C:10](=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=3)[CH:18]=[CH:17][CH:16]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 23295226HCID 23295226, compound2×

Product 1

HCID 135574102HCID 135574102, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(4-methoxyphenyl)quinoline (compound 28) (1.08 g) in methylene chloride (10 ml), a solution of boron tribromide in methylene chloride (1.0 M) (5.5 ml) was added at -40° C. under the inert atmosphere. The reaction mixture was stirred at room temperature for 15 hrs, then it was poured into a cooled solution of sodium hydrocarbonate (NaHCO3). The solution was extracted with ethyl acetate and then the organic layer was washed with satd. NH4Cl aq, water and brine. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The concentrate was crystallized with ethyl ether-methanol (10:1). The resulting precipitate was collected by filtration. 4-(quinoline-5-yl)phenol (29) was obtained as a yellow crystal (0.82 g).

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. washthe organic layer was washed with satd
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe concentrate was crystallized with ethyl ether-methanol (10:1)
  7. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-1db318710c64482fa03cc825030f6e1e
Source dataset
uspto-grants-2000_09
Patent number
US06124460

Reaction notes

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