Benzyl Bromide → HCID 21468867, compound

HRID 1938611Notes

Reaction equation

HRID 1938611 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)#[N:2].C([Mg]Br)C.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[CH2:22]([C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]#[N:2])[CH:10]=2)[NH:14][CH:13]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 25517Ammonium ChlorideHCID 21468934HCID 21468934, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 21468867HCID 21468867, compoundYield 32.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

5-(2-Cyanophenyl)indole (2.3 mmole, 0.50 g) was dissolved in 3 ml THF, cooled to 0° C. Ethyl magnesium bromide (2.41 mmoles, 1.21 ml of 2.0M solution in ether) was added dropwise. Benzyl bromide (94.6 mmole, 0.80 g) was added dropwise to the solution. The reaction was refluxed for 24 hours and poured into aqueous ammonium chloride and ethyl acetate. The organic phase was washed with water, dried over sodium sulfate, and concentrated. The intermediate was chromatographed over silica gel eluted with 10% ethyl acetate in hexane to yield 229 mg of 3-benzyl-5-(2-cyanophenyl)indole.

Workup

  1. temperatureThe reaction was refluxed for 24 hours
  2. washThe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe intermediate was chromatographed over silica gel
  6. washeluted with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-60885c1a829e4b83803743225371a231
Source dataset
uspto-grants-1997_12
Patent number
US05693633

Reaction notes

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