Dimethylformamide → 4-(4-Bromo-3-(1,3-dioxolan-2-yl)phenoxy)-3-chlorobenzonitrile

HRID 1255609Notes

Reaction equation

HRID 1255609 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1C#N.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=1[CH:19]1[O:23][CH2:22][CH2:21][O:20]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.O.C[N:38]([CH3:41])C=O>>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:3]2[CH:6]=[CH:7][C:8]([C:41]#[N:38])=[CH:9][C:2]=2[Cl:1])=[CH:14][C:13]=1[CH:19]1[O:20][CH2:21][CH2:22][O:23]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1090002-Chloro-4-fluorobenzonitrileHCID 22728543Water ethylacetateHCID 579687074-Bromo-3-(1,3-dioxolan-2-yl)phenol

Product 1

HCID 674417784-(4-Bromo-3-(1,3-dioxolan-2-yl)phenoxy)-3-chlorobenzonitrile

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-4-fluorobenzonitrile (4.43 g, 28.4 mmol), 4-bromo-3-(1,3-dioxolan-2-yl)phenol (6.96 g, 28.4 mmol), and potassium carbonate (4.70 g, 34.1 mmol) in N,N-dimethylformamide (60 mL) was stirred at 100° C. under nitrogen atmosphere overnight. The mixture was poured into ethyl acetate/water. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to give crude 4-(4-bromo-3-(1,3-dioxolan-2-yl)phenoxy)-3-chlorobenzonitrile (10.8 g), which was used for the next step without purification.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried on anhydrous sodium sulfate
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fa6156bf2854430b826976adde03d6b8
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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