1-Bromo-3-chloropropane → HCID 86755446, compound

HRID 1420706Notes

Reaction equation

HRID 1420706 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH3:2].[H-].[Na+].[Br:18][CH2:19][CH2:20][CH2:21][Cl:22]>CN(C=O)C>[Cl:22][CH2:21][CH2:20][CH2:19][N:7]1[C:6]2[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2.[Br:18][CH2:19][CH2:20][CH2:21][N:7]1[C:6]2[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 521706HCID 521706, compound

Product 1

HCID 86755446HCID 86755446, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound was synthesized in the same manner as in example 1. Treatment of 3-ethylcarbazole (2.0 g, 0.0102 mol) with NaH (0.27 g, 0.0112 mol) succeeded by the addition of 1-bromo-3-chloropropane (1.77 g, 0.0112 mol) in DMF gave the title compound 2.3 g (82%) as a yellow oil. 1H-NMR (δ, CDCl3): 1.35 (t, 3H); 2.4 (m, 2H); 2.8 (q, 2H); 3.35 (t, 1H); 3.45 (t, 1H); 4.35 (t, 2H); 7-7.4 (m, 4H); 7.9 (s, 2H); 8.1 (d, 2H). The product was isolated as an 1:1 mixture of the 3-bromo- and 3-chloro derivatives.

Workup

  1. customThe compound was synthesized in the same manner as in example 1

Sources & evidence

ORD record
ord-6cd72a111d9047b797731c9495aa0aab
Source dataset
uspto-grants-2000_06
Patent number
US06071932

Reaction notes

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