Dichloromethane → HCID 22995923, compound

HRID 1167177Notes

Reaction equation

HRID 1167177 reaction equation
B(Br)(Br)Br.[C:5]1([C:11]2(C)[CH:20]=[CH:19][C:18]3[C:13](=[C:14]([O:21]C)[CH:15]=[CH:16][CH:17]=3)[NH:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:24](Cl)Cl>>[C:5]1([C:11]2[C:20]([CH3:24])=[CH:19][C:18]3[C:13](=[C:14]([OH:21])[CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 229959212-Phenyl-2-methyl-8-methoxyquinoline

Product 1

HCID 22995923HCID 22995923, compoundYield 64%

Procedure

17.6 ml (180 mmol) of boron tribromide are added dropwise, at −30° C., to a solution of 21.2 g (85 mmol) of 2-phenyl-2-methyl-8-methoxyquinoline in 500 ml of methylene chloride. The cooling bath is then removed and the reaction medium is stirred for 3 hours until it has returned to ambient temperature. The reaction mixture is then poured onto ice and the medium is basified using sodium hydrogencarbonate. The medium is subsequently extracted with 3×200 ml of methylene chloride. The organic phases are combined, dried over magnesium sulfate, filtered and evaporated under vacuum. The residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane 3/7) to give 12.7 g of 2-phenyl-3-methyl-8-hydroxyquinoline in the form of a colorless oil. (Yield: 64%)

Workup

  1. customThe cooling bath is then removed
  2. customhas returned to ambient temperature
  3. additionThe reaction mixture is then poured onto ice
  4. extractionThe medium is subsequently extracted with 3×200 ml of methylene chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customThe residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane 3/7)

Sources & evidence

ORD record
ord-f06e63ad34494466a5163d79a1b23f5e
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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