Benzyl Bromide → HCID 18476208, compound

HRID 2187662Notes

Reaction equation

HRID 2187662 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[CH:5]2.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[K+]>C1OCCOCCOCCOCCOCCOC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]([CH3:11])=[CH:5]2

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 706365-Chloro-2-methylindole

Product 1

HCID 18476208HCID 18476208, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 2855718-Crown-6Catalyst

Procedure

4.97 g (30 mmol) 5-chloro-2-methylindole was treated with 6.84 g (40 mmol) benzyl bromide, 1.97 g (30 mmol) potassium hydroxide (85% powdered in mortar) and 0.25 g (1 mmol) 18-crown-6 as described in Synthesis 1979, p. 618 to give 3.22 g (42%) 5-chloro-2-methyl-1-benzyl-1H-indole, mp: 75-76°, MS (Ei 70 eV) m/Z M+255.

Workup

  1. customas described in Synthesis 1979, p

Sources & evidence

ORD record
ord-d7c771836c3a4d82a4c52e0b6ddaaaaf
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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