Benzyl Bromide → HCID 59170319, compound

HRID 1445915Notes

Reaction equation

HRID 1445915 reaction equation
[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:17])[C:11]=2[CH:10]=[C:9]1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([O:17][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 107523601-Benzyl-2-methyl-1H-indol-4-ol

Product 1

HCID 59170319HCID 59170319, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-hydroxy-2-methyl indole 1 (50 g, 0.339 mole) was dissolved in anhydrous DMF (1 L). To the mixture sodium hydride 60% in mineral oil (27.9 g, 0.697 mole) was added. The mixture was left to stir at rt. for 1 h. To the mixture benzyl bromide (82.7 mL, 0.697 mole) was added drop-wise. The mixture was left to stir at room temperature for 18 h. The reaction was diluted with ethyl acetate (4 L) and washed with water (5×500 mL) then brine (1 L). The organic layer was separated and dried with magnesium sulphate and concentrated. The orange oily residue was purified by column chromatography (6:1 Hexane:EtOAc) to afford 86 g (72%) of 2 as an yellow oil.

Workup

  1. waitThe mixture was left
  2. waitThe mixture was left
  3. stirringto stir at room temperature for 18 h
  4. washwashed with water (5×500 mL)
  5. customThe organic layer was separated
  6. dry with materialdried with magnesium sulphate
  7. concentrationconcentrated
  8. customThe orange oily residue was purified by column chromatography (6:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-28b1796b8ed24580b632c06a80ad5fe0
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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