Sodium Carbonate → HCID 46314397, compound

HRID 1723672Notes

Reaction equation

HRID 1723672 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.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>[Cl:10][C:4]1[CH:3]=[C:2]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[F:11])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 70104204-Bromo-2-chlorobenzonitrile

Product 1

HCID 46314397HCID 46314397, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-bromo-2-chlorobenzonitrile (2.2 g, 10 mmol) and 2-fluorobenzeneboronic acid (1.82 g, 13 mmol) in tetrahydrofuran (30 ml) was treated with 2M sodium carbonate (13 ml) then degassed with nitrogen for 10 min. Tetrakis(triphenylphosphine)palladium(0) (0.58 g, 0.5 mmol) was added and this mixture was heated under reflux for 12 h. The resulting mixture was partitioned between dichloromethane and water. The organics were washed with water, brine, dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo. Purification of the residue by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (5-15%) gave 3-chloro-2′-fluorobiphenyl-4-carbonitrile as a white solid (2.3 g, 99%): δH (400 MHz, CDCl3) 7.17-7.57 (5H, m), 7.64-7.75 (2H, m).

Workup

  1. customthen degassed with nitrogen for 10 min
  2. temperaturethis mixture was heated
  3. temperatureunder reflux for 12 h
  4. customThe resulting mixture was partitioned between dichloromethane and water
  5. washThe organics were washed with water, brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (5-15%)

Sources & evidence

ORD record
ord-e8d80a6398e541c6946dca26df45ce83
Source dataset
uspto-grants-2009_02
Patent number
US07485640B2

Reaction notes

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