Pyridine → 3-Bromo-5-chlorobenzamide

HRID 70282Notes

Reaction equation

HRID 70282 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5](O)=[O:6].[N:12]1C=CC=CC=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>CC#N>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([NH2:12])=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 331283-Bromo-5-chlorobenzoic acidHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 534174713-Bromo-5-chlorobenzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-bromo-5-chlorobenzoic acid (2.88 g; 12.2 mmol; Note 1) and pyridine (1.04 mL; 12.8 mmol) in MeCN (100 mL) at room temperature was added (Boc)2O (3.47 g; 15.9 mmol) in one portion. The mixture was aged 30 min, (NH4)2CO3 was added in one portion.

Sources & evidence

ORD record
ord-5fd7fbd0c56e41619fe134cf08fc6fa0
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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