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

HRID 2425565Notes

Reaction equation

HRID 2425565 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 tert-butoxide (628 mg, 5.60 mmol) in dry THF (10 ml) with ice cooling. The mixture was then allowed to warm to room temperature. After 2 hours at room temperature, to this was added a solution of 1-(6-bromoquinolin-2-yl)ethanone (Step CA1B) (700 mg, 2.80 mmol) in dry THF (15 ml) with ice-cooling then the mixture was allowed to warm to room temperature. 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 MHz, CDCl3) δ 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. temperatureto warm to room temperature
  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-63b0f01ec4ec4eaea1328f8df8e01111
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

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