6-Chloro-2-picoline → HCID 17933273, compound

HRID 861138Notes

Reaction equation

HRID 861138 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:5]([O:7]CC)=O.[Cl:15][C:16]1[N:21]=[C:20]([CH3:22])[CH:19]=[CH:18][CH:17]=1>>[Br:1][C:2]1[CH:3]=[C:4]([C:5](=[O:7])[CH2:22][C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:15])[N:21]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]

Participants

3

Reactant 2

HCID 876016-Chloro-2-picolineHCID 23062539Ethyl 3-bromo-4-methoxybenzoate

Product 1

HCID 17933273HCID 17933273, compoundYield 88.4%

Procedure

In a similar manner as described in Example 1 from ethyl 3-bromo-4-methoxybenzoate (13.6 g, 52.5 mmol) and 6-chloro-2-picoline (5.7 mL, 52.5 mmol), 1-(3-bromo-4-methoxyphenyl)-2-(6-chloro-2-pyridinyl)ethanone (15.8 g, 88%) was obtained as a yellow solid (existing as a mixture of ketone and enol tautomers). 1H NMR (CDCl3) of the ketone: δ 8.27 (s, 1H), 8.02 (dd, 1H), 7.63 (t, 1H), 7.23 (m, 2H), 6.94 (d, 1H), 4.41 (s, 2H), 3.97 (s, 3H); MS m/z340 (M+1).

Sources & evidence

ORD record
ord-a8e6052dfc20426a96fc0e618ace4625
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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