5-Bromonicotinoyl chloride → 3-Acetyl-5-bromopyridine

HRID 555998Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH3:11][Mg+].[Br-]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:6]([C:7](=[O:8])[CH3:11])[CH:5]=[N:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

5-Bromo-nicotinoyl chloride (0.5 g, 2.268 mmol) is suspended in THF (24 ml) at room temperature under an atmosphere of Argon. Fe(acac)3 (0.04 g, 0.113 mmol) is added and the reaction mixture is stirred for 10 minutes until a solution forms. The reaction mixture is cooled to −78° C. and a solution of MeMgBr (3M in diethyl ether, 0.907 ml, 2.722 mmol) is added dropwise with stirring for 2 hours at −78° C. On warming to room temperature silica is added to the reaction mixture and the solvents are reduced in vacuo. Purification by flash chromatography eluting with 50:50 EtOAc/iso-hexanes affords the title compound as a yellow solid [MH+199.90 and 201.90].

Workup

stirringwith stirring for 2 hours at −78° C
temperatureOn warming to room temperature silica
additionis added to the reaction mixture
customPurification by flash chromatography
washeluting with 50:50 EtOAc/iso-hexanes

Sources & evidence

ORD record: ord-d73c4c2584aa438ba0990cfaab4bfe03
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053574B2

Reaction notes

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