Potassium tert-butoxide → 6-Bromo-2-isopropenylquinoline

HRID 1094653Notes

Reaction equation

HRID 1094653 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([C:18](=O)[CH3:19])[CH:12]=[CH:11]2>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([C:18]([CH3:19])=[CH2:1])[CH:12]=[CH:11]2

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 574581651-(6-Bromoquinolin-2-yl)ethanone

Product 1

HCID 666370726-Bromo-2-isopropenylquinolineYield 95.1%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred suspension of (methyl)triphenylphosphonium bromide (2000 mg, 5.60 mmol) in dry THF (15 ml) was added a solution of potassium t-butoxide (628 mg, 5.60 mmol) in dry THF (10 ml) at ice-cooling. After 2 hours at room temperature, to this was added a solution of 1-(6-bromoquinolin-2-yl)ethanone (700 mg, 2.80 mmol) in dry THF (15 ml) at ice-cooling. After 3 hours at ambient temperature, the mixture was quenched with water and extracted with ethyl acetate (×2). The combined solution was washed with brine, dried over sodium sulfate and concentrated in vacuo to give crude product, which was purified by column chromatography on silica gel (250 g) with hexane-ethyl acetate (10:1) to furnish the title compound (661 mg, 95%) as a tan solid. 1H NMR (270 MH CDCl3) δ ppm 2.34 (3H, s), 5.50 (1H, s), 5.93 (1H, s), 7.65-7.78 (2H, m), 7.88-8.03 (3H, m). MS (ESI): m/z 248.11, 250.14 (M+H)+.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. waitAfter 3 hours at ambient temperature
  4. customthe mixture was quenched with water
  5. extractionextracted with ethyl acetate (×2)
  6. washThe combined solution was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give crude product, which
  10. customwas purified by column chromatography on silica gel (250 g) with hexane-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-b4cadb60b4f54b1885a155e253997a9d
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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