Benzyl Bromide → HCID 18536110, compound

HRID 412177Notes

Reaction equation

HRID 412177 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCOC(C)=O>CN(C=O)C.O>[CH2:19]([O:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([I:1])[CH:3]=[CH:4][CH:5]=2)[CH:10]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 6229868-Iodo-2-naphthol

Product 1

HCID 18536110HCID 18536110, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Step A (1.18 g, 4.37 mmol) in 20 mL of DMF was added cesium carbonate (2.48 g, 8.74 mmol) and benzyl bromide (0.52 mL, 4.37 mmol). After stirring overnight at room temperature, the reaction was poured into EtOAc and water, washed with 5% NaOH solution, water, 10% NaHSO3 solution and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (5% EtOAc/hexane) to yield the desired product as a pink solid.

Workup

  1. washwashed with 5% NaOH solution, water, 10% NaHSO3 solution and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (5% EtOAc/hexane)

Sources & evidence

ORD record
ord-86f5cca8b73440de919046b7a84d9fb0
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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