Benzyl Bromide → HCID 15524285, compound

HRID 1744000Notes

Reaction equation

HRID 1744000 reaction equation
[CH2:1]([Br:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[C:16]([O:19][CH2:20][CH3:21])(=O)[CH3:17].[CH2:22](Cl)Cl.[CH3:25][CH2:26][CH2:27][CH2:28][CH2:29]C>C(#N)C>[Br:8][C:1]1[C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[C:16]([O:19][CH2:20][C:21]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:17][CH:22]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21226440Methylenechloride HexaneHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 15524285HCID 15524285, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The above oil was dissolved in 100 mL acetonitrile, and treated with 3.57 mL (30 mmol) benzyl bromide and 5.53 g (40 mmol) potassium carbonate, the refluxed 14 h. TLC showed a major spot at Rf=0.3 in 10% methylene chloride/hexane (with benzyl bromide at Rf=0.4). The reaction was cooled, poured into dilute aqueous hydrochloric acid/ethyl acetate, and the organic layer separated, washed with water and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using methylene chloride/hexane as eluant to afford 4.0 g (63%) of an oil.

Workup

  1. customthe refluxed 14 h
  2. temperatureThe reaction was cooled
  3. customthe organic layer separated
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-30a8ab4ff0124868a4b7462bbb2679ba
Source dataset
uspto-grants-2006_03
Patent number
US07012078B2

Reaction notes

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