Azobisisobutyronitrile → 6-(Bromomethyl)pyridine-3-carbonitrile

HRID 1506602Notes

Reaction equation

[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[Br:10]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClCCCl>[Br:10][CH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 6-methylnicotinonitrile (1.0 g, 8.47 mmol) in 1,2-dichloroethane (30 mL) was added N-bromosuccinimide (NBS; 1.52 g, 8.54 mmol) and followed by 2,2′-azobis(isobutyronitrile) (AIBN; 0.14 g, 0.85 mmol) at RT. The reaction mixture was then heated to 80° C. and stirred for 14 h. After complete consumption of the starting material (by TLC), the reaction mixture was cooled to RT, and the volatiles were removed under reduced pressure to obtain the crude material. Purification by silica gel column chromatography eluting with 10% EtOAc/Hexane) afforded compound I-4 (0.6 g, 3.05 mmol, 36%) as a colorless liquid. 1H NMR (500 MHz, CDCl3): δ 7.67-7.62 (m, 2H), 7.21 (dd, J=9.0, 2.0 Hz, 1H), 4.44 (s, 2H).

Workup

customAfter complete consumption of the starting material (by TLC)
temperaturethe reaction mixture was cooled to RT
customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record: ord-4c7198fc906e43309ce389e64738ef7e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09220265B2

Reaction notes

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