Benzyl Bromide → HCID 70052329, compound

HRID 363052Notes

Reaction equation

HRID 363052 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[C:24]1([CH2:23][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]3[CH:10]=[CH:11][C:12]([C:13]#[N:14])=[CH:15][CH:16]=3)=[CH:6][CH:7]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 21200954HCID 21200954, compound

Product 1

HCID 70052329HCID 70052329, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 26-4 (0.105 g, 0.50 mmol) and cesium carbonate (0.326 g, 1.0 mmol) in dimethylformamide (1 ml) under nitrogen was added benzyl bromide (0.071 ml, 0.60 mmol). The mixture was stirred 18 h at ambient temperature. The resulting mixture was evaporated under reduced pressure. To the residue was added saturated sodium bicarbonate solution (15 ml), and the aqueous mixture was extracted with methylene chloride (2×30 ml). The organic fraction was washed with brine (10 ml), dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/hexane (1:6 increasing to 1:5), to give a white solid. The solid was recrystallized from ethyl acetate/hexane to give product 26-5 as white crystals, mp: 110°-111° C.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. additionTo the residue was added saturated sodium bicarbonate solution (15 ml)
  3. extractionthe aqueous mixture was extracted with methylene chloride (2×30 ml)
  4. washThe organic fraction was washed with brine (10 ml)
  5. dry with materialdried (sodium sulfate)
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with ethyl acetate/hexane (1:6 increasing to 1:5)
  9. customto give a white solid
  10. customThe solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4fcffe3d044242caa7100486c6101e78
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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