Benzyl Bromide → HCID 15524285, compound

HRID 842045Notes

Reaction equation

HRID 842045 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, then refluxed 14 hours. Thin layer chromatography (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. 1H-NMR (δ, CDCl3): 1.77 (m, 4H), 2.75 (m, 4H), 5.045 (s, 2H), 6.62 (d, J=9, 1H), 7.3-7.5 (m, 6H); 13C-NMR (δ, CDCl3): 22.2, 22.9, 24.0, 30.7, 69.9, 109.8, 116.7, 127.1, 127.9, 128.6, 129.1, 129.3, 137.2, 137.5, 155.6.

Workup

  1. temperaturerefluxed 14 hours
  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-5131855a79ff4e989f5c1fca28f10d89
Source dataset
uspto-grants-2002_04
Patent number
US06372768B1

Reaction notes

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