1,2-Dimethoxyethane → HCID 66924340, compound

HRID 1364426Notes

Reaction equation

HRID 1364426 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](I)[C:3]=1[C:4]#[N:5].[Cl:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:11][C:12]1[CH:17]=[C:16]([C:6]2[C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=[CH:8][CH:7]=2)[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 5227222-Fluoro-6-iodobenzonitrileHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 66924340HCID 66924340, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

In a dry round bottom flask were added 2-fluoro-6-iodobenzonitrile (500 mg; 2.02 mmol), 3-chlorophenyl boronic acid (380 mg; 2.43 mmol), sodium carbonate (2.32 g; 21.86 mmol), tetrakis(triphenylphosphine)palladium(0) (77 mg; 0.07 mmol), DME (20 mL) and water (20 mL) and heated to reflux for 8 hours. The reaction mixture was cooled to room temperature and extracted with ethyl acetate (3×), washed with brine (1×) and water (1×). Organic layers were combined and dried over sodium sulfate and then filtered and solvent removed to yield crude material which was purified by column chromatography (4% ethyl acetate/hexane) to obtain 150 milligrams of 3′-chloro-3-fluorobiphenyl-2-carbonitrile.

Workup

  1. temperatureheated
  2. temperatureto reflux for 8 hours
  3. extractionextracted with ethyl acetate (3×)
  4. washwashed with brine (1×) and water (1×)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customsolvent removed
  8. customto yield crude material which
  9. customwas purified by column chromatography (4% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fba3d73d9ce549a49938e78c20b8fa1d
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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