4-Fluorophenol → 3-Bromo-5-(4-fluorophenoxy)benzonitrile

HRID 40749Notes

Reaction equation

HRID 40749 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16](F)[CH:17]=1)[C:13]#[N:14].C([O-])([O-])=O.[K+].[K+]>CN(C)C(=O)C.CCOC(C)=O.O>[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:17]=1)[C:13]#[N:14]

Participants

7

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 27833303-Bromo-5-fluorobenzonitrile

Product 1

HCID 595880633-Bromo-5-(4-fluorophenoxy)benzonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-fluorophenol (0.3 g, 2.7 mmol), 3-bromo-5-fluorobenzonitrile (0.53 g, 2.7 mmol), K2CO3 (1.1 g, 8.0 mmol) in N,N-dimethylacetamide (3 mL) was heated to 160° C. for 3 hr. The reaction mixture was cooled to room temperature and diluted with EtOAc and water. The organic layer was separated, dried (MgSO4), concentrated, and purified by chromatography on silica gel (EtOAc/hexanes) to afford 3-bromo-5-(4-fluorophenoxy)benzonitrile.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by chromatography on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-bed3cd8e8a5b4c08b42837b1b89537c6
Source dataset
uspto-grants-2013_09
Patent number
US08530480B2

Reaction notes

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