6-Chloro-2-picoline → HCID 17933279, compound

HRID 861140Notes

Reaction equation

HRID 861140 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[C:5]([O:7]CC)=O.[Cl:14][C:15]1[N:20]=[C:19]([CH3:21])[CH:18]=[CH:17][CH:16]=1>>[Br:1][C:2]1[CH:3]=[C:4]([C:5](=[O:7])[CH2:21][C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:14])[N:20]=2)[CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

3

Reactant 2

HCID 876016-Chloro-2-picolineHCID 12594300Ethyl 3-bromo-4-chlorobenzoate

Product 1

HCID 17933279HCID 17933279, compound

Procedure

In a similar manner as described in Example 1 from ethyl 3-bromo-4-chlorobenzoate (42.6 g, 171 mmol) and 6-chloro-2-picoline (18.7 mL, 171 mmol), 1-(3-bromo-4-chlorophenyl)-2-(-6-chloro-2-pyridinyl)ethanone was obtained as a pale yellow solid existing as a mixture of ketone and enol tautomers. 1H NMR (CDCl3) of ketone: δ 8.30 (d, 1H), 7.92 (dd, 1H), 7.69–7.54 (m, 2H), 7.24 (m, 2H), 4.42 (s, 2H); MS m/z 344 (M+1).

Sources & evidence

ORD record
ord-b63059e0314f4d00bd30b900d0490cd1
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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