Phosphonium, (bromomethyl)triphenyl-, bromide (1:1) → (Z)-2-(2-bromovinyl)-6-fluoroquinoline

HRID 920896

Reaction equation

HRID 920896 reaction equation
[Br-].[Br:2][CH2:3][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[F:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[N:36]=[C:35]([CH:40]=O)[CH:34]=[CH:33]2>C1COCC1>[Br:2]/[CH:3]=[CH:40]\[C:35]1[CH:34]=[CH:33][C:32]2[C:37](=[CH:38][CH:39]=[C:30]([F:29])[CH:31]=2)[N:36]=1

Participants

5

Reactant 3

HCID 2733422Phosphonium, (bromomethyl)triphenyl-, bromide (1:1)HCID 31596056-Fluoroquinoline-2-carbaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 86683113(Z)-2-(2-bromovinyl)-6-fluoroquinolineYield 65.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To as suspension of (bromomethyl)triphenylphosphonium bromide (14.94 g, 34.3 mmol) in 100 mL of THF was added potassium tert-butoxide (3.84 g, 34.3 mmol) portionwise under Ar. Then the reaction mixture was stirred for 1 h at this temperature. 6-Fluoroquinoline-2-carbaldehyde (5 g, 28.5 mmol) in 40 mL of THF was added. The resulting reaction mixture was stirred for 5 h at −75° C. and allowed to warm up overnight. The reaction mixture was diluted with petrol ether and the solid was sucked off. The mother liquid was concentrated, diisopropyl ether was added and the formed precipitate was sucked off. The mother liquid was purified by column chromatography (cyclohexane/EA) to give 4.7 g (65.3%) of the title compound as brown solid. LC-MS: m/e 254.0.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 5 h at −75° C.
  3. temperatureto warm up overnight
  4. concentrationThe mother liquid was concentrated
  5. additiondiisopropyl ether was added
  6. customThe mother liquid was purified by column chromatography (cyclohexane/EA)

Sources & evidence

ORD record
ord-20c5ec6bafca4fb0a9ce6892d8c2c734
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Linked notes

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