Solketal → HCID 71256971, compound

HRID 927320Notes

Reaction equation

HRID 927320 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[Br:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH2:25][CH2:26][CH2:27]Br)[C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][C:19]([Br:24])=[CH:18][CH:17]=3>COCCOC>[Br:24][C:19]1[CH:18]=[CH:17][C:16]2[N:15]([CH2:25][CH2:26][CH2:27][O:8][CH2:7][CH:5]3[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]3)[C:14]3[C:22]([C:21]=2[CH:20]=1)=[CH:23][C:11]([Br:10])=[CH:12][CH:13]=3

Participants

4

Reactant 2

HCID 7528SolketalHCID 580972043,6-dibromo-9-(3-bromopropyl)-9H-carbazole

Product 1

HCID 71256971HCID 71256971, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Potassium terbutylate (0.8 g, 7.1 mmoles) are added, in an inert atmosphere, to a solution of solketal (0.9 g, 7.1 mmoles) in 10 ml of 1,2-dimethoxyethane. After 15 minutes, 3,6-dibromo-9-(3′-bromopropyl)carbazole (2.1 g, 4.7 mmoles) dissolved in 10 ml of 1,2-dimethoxyethane, are added dropwise. After hours, the 1,2-dimethoxyethane is removed by distillation at reduced pressure, the residue is recovered with water and extracted with ethyl acetate. After washing the organic phase with water until neutrality, said organic phase is anhydrified on sodium sulfate. The solvent is removed by distillation at reduced pressure. After purification by elution on an alumina column (heptane/ethyl acetate=9/1), 1.6 g of 3,6-dibromo-9-{(3-[(2,2-dimethyl-1,3-di-oxolan-4-yl)methoxy]propyl}-9H-carbazole are obtained (yield=70%).

Workup

  1. additionare added dropwise
  2. waitAfter hours
  3. customthe 1,2-dimethoxyethane is removed by distillation at reduced pressure
  4. customthe residue is recovered with water
  5. extractionextracted with ethyl acetate
  6. washAfter washing the organic phase with water until neutrality
  7. customThe solvent is removed by distillation at reduced pressure
  8. customAfter purification
  9. washby elution on an alumina column (heptane/ethyl acetate=9/1), 1.6 g of 3,6-dibromo-9-{(3-[(2,2-dimethyl-1,3-di-oxolan-4-yl)methoxy]propyl}-9H-carbazole
  10. customare obtained (yield=70%)

Sources & evidence

ORD record
ord-3a70ca6508fc4cabbdab34bb70685783
Source dataset
uspto-grants-2016_03
Patent number
US09290483B2

Reaction notes

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