N-bromobutanimide → 3-{[3-(Bromomethyl)-2-chloro-6-fluorophenyl]oxy}-5-chlorobenzonitrile

HRID 1875127Notes

Reaction equation

HRID 1875127 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:16]([F:17])=[CH:15][CH:14]=[C:13]([CH3:18])[C:12]=2[Cl:19])[CH:9]=1)[C:5]#[N:6].C1C(=O)N([Br:27])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:27][CH2:18][C:13]1[C:12]([Cl:19])=[C:11]([O:10][C:8]2[CH:7]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:9]=2)[C:5]#[N:6])[C:16]([F:17])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 684836723-Chloro-5-[(2-chloro-6-fluoro-3-methylphenyl)oxy]benzonitrile

Product 1

HCID 684854633-{[3-(Bromomethyl)-2-chloro-6-fluorophenyl]oxy}-5-chlorobenzonitrileYield 61.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

The title compound was prepared as described herein using 3-chloro-5-[(2-chloro-6-fluoro-3-methylphenyl)oxy]benzonitrile (940 mg, 3.17 mmol), NBS (593 mg, 3.33 mmol) and AIBN (26.1 mg, 0.159 mmol) in CCl4 (30.0 ml) to give the title compound as a white solid (728 mg, 61%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.41 (1H, dd, J=8.7, 5.3 Hz) 7.36 (1H, s) 7.18 (1H, s) 7.12-7.16 (1H, m) 6.99 (1H, s) 4.58 (2H, s). LCMS: m/z 375 (M+1).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-653a191f65764a5ba64f2dc6ba7c794e
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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