Tetrabutylammonium Fluoride → 5-Bromo-2-methyl-8-quinolinol

HRID 2393099Notes

Reaction equation

HRID 2393099 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Br:19][C:20]1[CH:29]=[CH:28][C:27]([O:30][Si](C(C)(C)C)(C)C)=[C:26]2[C:21]=1[CH:22]=[CH:23][C:24]([CH3:38])=[N:25]2>O1CCCC1.ClCCl>[Br:19][C:20]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]2[C:21]=1[CH:22]=[CH:23][C:24]([CH3:38])=[N:25]2

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10594137HCID 10594137, compound

Product 1

HCID 109555895-Bromo-2-methyl-8-quinolinol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (54 ml, 1M in tetrahydrofuran) was added dropwise to a stirred solution of 5-bromo-8-t-butyldimethylsilyloxyquinaldine (16.3 g) in tetrahydrofuran (500 ml). After stirring for 10 minutes the reaction was diluted with dichloromethane (500 ml) and extracted with water (3×200 ml). The organic phase was dried over magnesium sulphate and concentrated in vacuo. Purification by recrystallisation from aqueous methanol afforded the title compound as an off white solid (7.7 g).

Workup

  1. extractionextracted with water (3×200 ml)
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customPurification
  5. customby recrystallisation from aqueous methanol

Sources & evidence

ORD record
ord-722d2e4482564672b04ea4f732b2b774
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

Loading…