Water → HCID 10125263, compound

HRID 585582Notes

Reaction equation

HRID 585582 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]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>CN(C=O)C.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:15]2[CH:14]=[CH:13][C:12]([F:11])=[CH:17][C:16]=2[F:18])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27343342,4-Difluorophenylboronic acidHCID 70104204-Bromo-2-chlorobenzonitrile

Product 1

HCID 10125263HCID 10125263, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

In a round bottom flask, 4-bromo-2-chlorobenzonitrile (3 g, 13.85 mmol), 2,4-difluorophenylboronic acid (2.63 g, 16.63 mmol) and K3PO4 (8.83 g, 41.56 mmol) were added in dry DMF (50 mL). The mixture was purged under argon for 30 min and Pd(PPh3)4 (1.6 g, 1.38 mmol) was added. The mixture was heated for 48 hr at 80 C. Water (100 mL) was added and the aq layer was extracted with CH2Cl2 (3×50 mL). The organic layer was washed with brine (3×50 mL), dried, evaporated and purified on silica gel (EtOAc/hexanes:1/19) to give the product (1 g, 29%), 1H.NMR (acetone-d6) δ: 7.2-7.28 (m, 2H), 7.72-7.79 (m, 2H), 7.91 (t, 1H, J=1.4 Hz), 8.02 (d, 1H, J=8.1 Hz).

Workup

  1. customThe mixture was purged under argon for 30 min
  2. temperatureThe mixture was heated for 48 hr at 80 C
  3. extractionthe aq layer was extracted with CH2Cl2 (3×50 mL)
  4. washThe organic layer was washed with brine (3×50 mL)
  5. customdried
  6. customevaporated
  7. custompurified on silica gel (EtOAc/hexanes:1/19)

Sources & evidence

ORD record
ord-7e2b6d5595f4405db9fcc943e3ec3c38
Source dataset
uspto-grants-2005_08
Patent number
US06933321B2

Reaction notes

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