Ethyl 4-bromobenzoate → HCID 17933282, compound

HRID 861115Notes

Reaction equation

HRID 861115 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=O)=[CH:4][CH:3]=1.[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]=[CH:4][C:5]([C:6](=[O:8])[CH2:20][C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:13])[N:19]=2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 22043Ethyl 4-bromobenzoateHCID 876016-Chloro-2-picoline

Product 1

HCID 17933282HCID 17933282, compoundYield 82%

Procedure

In a similar manner as described in Example 1, from ethyl 4-bromobenzoate (12.8 mL, 78.3 mmol) and 6-chloro-2-picoline (4.3 mL, 39.2 mmol), 1-(4-bromophenyl)-2-(6-chloro-2-pyridinyl)ethanone (9.6 g, 82%) was obtained as a crystalline solid existing as a keto-enol tautomeric mixture. 1H NMR (CDCl3): for the keto tautomer δ 7.95 (d, 2H), 7.74–7.56 (m, 3H), 7.27 (m, 2H), 4.47 (s, 2H); MS m/z 310 (M+1).

Sources & evidence

ORD record
ord-c559987895ad423b8c3d66615e72f05a
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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