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

HRID 1875096Notes

Reaction equation

HRID 1875096 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[F: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]([F: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 684866063-Chloro-5-[(2,6-difluoro-3-methylphenyl)oxy]benzonitrile

Product 1

HCID 684853683-{[3-(Bromomethyl)-2,6-difluorophenyl]oxy}-5-chlorobenzonitrileYield 56%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 3-chloro-5-[(2,6-difluoro-3-methylphenyl)oxy]benzonitrile (4.05 g, 14.48 mmol) and NBS (3.09 g, 17.38 mmol) in carbon tetrachloride (500 mL) was degassed and heated to 90° C. under a nitrogen atmosphere. After ca. 5 min, AIBN (0.119 g, 0.724 mmol) was added and the solution was heated for 6 h. The solution was cooled to 0° C. then filtered through Celite. The filtrate was concentrated and the crude material was purified on silica gel (hexanes/ethyl acetate) to give the title compound (2.9 g, 56%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.31-7.40 (m, 2H), 7.21 (t, 1H), 7.04-7.11 (m, 2H), 4.51 (s, 2H).

Workup

  1. temperaturethe solution was heated for 6 h
  2. temperatureThe solution was cooled to 0° C.
  3. filtrationthen filtered through Celite
  4. concentrationThe filtrate was concentrated
  5. customthe crude material was purified on silica gel (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-ac9418daef9340c2b5ef82ebef08afa9
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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