Benzyl Bromide → HCID 131726143, compound

HRID 857362Notes

Reaction equation

HRID 857362 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH:5]1[C:9]2=[CH:10][C:11]3[C:12]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:13][C:14]([OH:17])=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+].[NH4+].[Cl-]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH:5]1[C:9]2=[CH:10][C:11]3[C:12]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:13][C:14]([O:17][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 58760708HCID 58760708, compound

Product 1

HCID 131726143HCID 131726143, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the alcohol from Step 2 (0.19 g, 0.59 mmol) and benzyl bromide (0.10 mL, 0.88 mmol) in DMF (4 mL) at 0° C. was added Cs2CO3 (0.29 g, 0.88 mmol). The mixture was stirred at RT for 1 hour, and then saturated NH4Cl solution and H2O were added. The product was extracted with 1:1 EtOAc:Et2O and the organic layer was washed with H2O and brine. After drying (MgSO4), filtering, and removal of solvent, the crude product was purified by flash chromatography (1:2 EtOAc:hexane) to give a tan coloured foam (0.23 g).

Workup

  1. extractionThe product was extracted with 1:1 EtOAc
  2. washEt2O and the organic layer was washed with H2O and brine
  3. dry with materialAfter drying (MgSO4)
  4. filtrationfiltering
  5. customremoval of solvent
  6. customthe crude product was purified by flash chromatography (1:2 EtOAc:hexane)

Sources & evidence

ORD record
ord-904ef0d30d704c5ea2f999f2e5559615
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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