Water → 4-((3,4-Dichlorophenoxy)methyl)-2,5-difluorobenzonitrile

HRID 508432Notes

Reaction equation

HRID 508432 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH2:10]Br)[C:7]([F:12])=[CH:6][C:3]=1[C:4]#[N:5].[Cl:13][C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[CH:18][C:19]=1[Cl:20].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][C:19]=1[Cl:20])[O:21][CH2:10][C:8]1[C:7]([F:12])=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 534042034-(Bromomethyl)-2,5-difluorobenzonitrile

Product 1

HCID 666676954-((3,4-Dichlorophenoxy)methyl)-2,5-difluorobenzonitrileYield 22%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2,5-difluoro-4-(bromomethyl)benzonitrile (Preparation 22, 530 mg, 2.30 mmol) and 3,4-dichlorophenol (375 mg, 2.30 mmol) in acetone (12 mL) was added potassium carbonate (954 mg, 6.90 mmol). The mixture was stirred at room temperature for 36 hours. The reaction mixture was then poured into water (25 mL) and extracted with EtOAc (3×25 mL). The combined organics were dried over sodium sulphate and evaporated to yield the crude product as a yellow oil, which was purified by silica gel chromatography eluting with 50% heptanes in DCM to afford the title compound as a white solid (153 mg, 22%).

Workup

  1. extractionextracted with EtOAc (3×25 mL)
  2. dry with materialThe combined organics were dried over sodium sulphate
  3. customevaporated
  4. customto yield the crude product as a yellow oil, which
  5. customwas purified by silica gel chromatography
  6. washeluting with 50% heptanes in DCM

Sources & evidence

ORD record
ord-f0132e2d53f743839d270dc56b1350b4
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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