Allyl bromide → HCID 16726256, compound

HRID 244427Notes

Reaction equation

HRID 244427 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[CH2:15](Br)[CH:16]=[CH2:17]>CN(C=O)C>[CH2:17]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=2)[CH:6]=[CH:7]1)[CH:16]=[CH2:15]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 6764936-BromoindoleHCID 178418361HCID 178418361, compound

Product 1

HCID 16726256HCID 16726256, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a room temperature solution of 10.0 g (51.0 mmol) of 6-bromoindole in DMF was added 1.4 g (58.0 mmol) of 60% NaH in mineral oil. Once evolution of hydrogen ceased, allyl bromide was added. After 2 hours, the reaction was quenched with water and was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford 11.8 g (98%) of 1-allyl-6-bromo-1H-indole. MS m/z 237.11 (MH+).

Workup

  1. customthe reaction was quenched with water
  2. extractionwas extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c8245b6bb894d0f8cd68795e67f2f70
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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