Benzyl Bromide → 1-Benzyl-5-chloro-1H-indole

HRID 2187660

Reaction equation

HRID 2187660 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[K+]>C1OCCOCCOCCOCCOCCOC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 871105-Chloroindole

Product 1

HCID 184763621-Benzyl-5-chloro-1H-indoleYield 60%

Reagents, catalysts & solvents 1

HCID 2855718-Crown-6Catalyst

Procedure

3.85 g (30 mmol) 5-chloroindole was treated with 6.84 g (40 mmol) benzylbromide, 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, giving 4.35 g (60%) 5-chloro-1-benzyl-1H-indole, yellow oil, MS (Ei 70 eV) m/Z M+241.

Workup

  1. customas described in Synthesis 1979 p

Sources & evidence

ORD record
ord-c8bb294274f149a486021e2c82c96850
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Linked notes

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