6-Chloro-2-picoline → HCID 17933269, compound

HRID 861122Notes

Reaction equation

HRID 861122 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7]CC)=O.[Cl:13][C:14]1[N:19]=[C:18]([CH3:20])[CH:17]=[CH:16][CH:15]=1>>[Br:1][C:2]1[CH:3]=[C:4]([C:5](=[O:7])[CH2:20][C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:13])[N:19]=2)[CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 876016-Chloro-2-picolineHCID 90488Ethyl 3-bromobenzoate

Product 1

HCID 17933269HCID 17933269, compoundYield 87%

Procedure

In a similar manner as described in Example 1 from ethyl 3-bromobenzoate (50.6 g, 220 mmol) and 6-chloro-2-picoline (24 mL, 220 mmol), 1-(3-bromophenyl)-2-(6-chloro-2-pyridinyl)ethanone (59.4 g, 87%) was obtained as a yellow solid. 1H NMR (CDCl3): δ 7.96 (broad s, 1H), 7.71 (d, 1H), 7.35–7.25 (m, 3H), 6.98 (t, 1H), 6.81 (d, 1H), 6.58 (d, 1H), 5.84 (s, 1H); MS m/z 310 (M+1).

Sources & evidence

ORD record
ord-1ed684a87cce4e52bde4eca1c6d3d351
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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