Benzyl Bromide → HCID 57672488, compound

HRID 2101789Notes

Reaction equation

HRID 2101789 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:15][CH2:16][CH3:17])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:15][CH2:16][CH3:17])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 57672400HCID 57672400, compound

Product 1

HCID 57672488HCID 57672488, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a flask containing 27.1 (0.900 g, 2.99 mmol) and cesium carbonate (1.27 g, 3.88 mmol) in 8 mL of DMF was added benzyl bromide (0.43 mL, 3.59 mmol), and the resulting mixture was stirred overnight. The reaction was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and then purified by silica gel chromatography (0 to 20% EtOAc/Hexanes) to provide 27.2 (1.00 g, 86% yield).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (0 to 20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-09bcb0ff26a848d18501e9f34aa7afbf
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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