Acetonitrile → 6-(4-Bromo-3-[1,3]dioxolan-2-yl-phenoxy)-2-chloro-nicotinonitrile 2-(4-bromo-3-[1,3]dioxolan-2-yl-phenoxy)-6-chloro-nicotinonitrile

HRID 1664367Notes

Reaction equation

HRID 1664367 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([Cl:15])[N:8]=2)=[CH:4][C:3]=1[CH:18]=[O:19].[Br:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[CH:28]1[O:32][CH2:31][CH2:30][O:29]1.C([O-])([O-])=O.[K+].[K+].[C:39](#[N:41])[CH3:40]>>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([Cl:15])[N:8]=2)=[CH:4][C:3]=1[CH:18]1[O:27][CH2:24][CH2:23][O:19]1.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:7]2[N:8]=[C:9]([Cl:15])[CH:10]=[CH:11][C:40]=2[C:39]#[N:41])=[CH:23][C:22]=1[CH:28]1[O:29][CH2:30][CH2:31][O:32]1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 579687074-Bromo-3-(1,3-dioxolan-2-yl)phenolHCID 866364296-(4-Bromo-3-formyl-phenoxy)-2-chloro-nicotinonitrile

Product 1

HCID 866364276-(4-Bromo-3-[1,3]dioxolan-2-yl-phenoxy)-2-chloro-nicotinonitrile 2-(4-bromo-3-[1,3]dioxolan-2-yl-phenoxy)-6-chloro-nicotinonitrile

Conditions

Temperature
65 °C

Procedure

To a solution of 2,6-dichloro-nicotinonitrile (3) (7.06 g, 40.8 mmol) in acetonitrile (anhydrous, 300 mL) were added 4-bromo-3-[1,3]dioxolan-2-yl-phenol (2) (10 g, 40.8 mmol) and K2CO3 (5.63 g, 40.8 mmol). The reaction was heated at 65° C. for 3 hours. The solution was filtered and evaporated in vacuo to afford 15.6 g of the product mixture. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.94 (d, J=9.0 Hz, 2H), 7.62 (d, J=8.6 Hz, 2H), 7.46 (d, J=3.1 Hz, 1H), 7.41 (d, J=3.1 Hz, 1H), 7.18-7.08 (m, 2H), 7.05 (dd, J=8.8, 2.93 Hz, 1H), 6.93 (d, J=8.2 Hz, 1H), 6.11 (s, 1H), 6.09 (s, 1H), 4.19-3.99 (m, 8H).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-52731310762e4e57be04306a63d054b1
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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