Benzoyl Peroxide → 6-(5-Bromomethylnaphthalen-1-yloxy)nicotinonitrile

HRID 2060860Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[O:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][N:14]=1.[Br:21]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[O:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][N:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 6-(5-methylnaphthalen-1-yloxy)nicotinonitrile (Preparation 22) (530 mg, 2.04 mmol) in carbon tetrachloride (30 mL) under argon was added N-bromosuccinimide (435 mg, 2.44 mmol) followed by benzoyl peroxide (25 mg, 0.1 mmol). The mixture was heated to 70° C. for 16 h. The reaction mixture was cooled, filtered through celite, and washed with DCM (70 mL). The organic phase was washed with NaHCO3 (30 mL), brine (30 mL) and dried (MgSO4). Solvent was removed in vacuo to give the title compound: RT=3.93 min; m/z (ES+)=341.0 [M+H]+.

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered through celite
washwashed with DCM (70 mL)
washThe organic phase was washed with NaHCO3 (30 mL), brine (30 mL)
dry with materialdried (MgSO4)
customSolvent was removed in vacuo

Sources & evidence

ORD record: ord-0536866a5ef94586961590a36ec47ba2
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278442B2

Reaction notes

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