Benzyl Bromide → HCID 59170319, compound

HRID 1445899Notes

Reaction equation

HRID 1445899 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:11])[NH:6]2.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:14]([N:6]1[C:7]2[C:3](=[C:2]([O:1][CH2:4][C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=3)[CH:10]=[CH:9][CH:8]=2)[CH:4]=[C:5]1[CH3:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5902254-Hydroxy-2-methylindole

Product 1

HCID 59170319HCID 59170319, compoundYield 155%

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-d7b840dc194e490182eb76f8312874da
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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