Sodium Carbonate → HCID 22254166, compound

HRID 1611705Notes

Reaction equation

HRID 1611705 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 27569932-Bromo-4-fluoro-1-nitrobenzene

Product 1

HCID 22254166HCID 22254166, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

The mixture containing 1-bromo 5-fluoro 2-nitrobenzene (1 g, 4.5 mmol), 2,4-dichloro benzeneboronicacid (907 mg, 4.7 mmol), sodiumcarbonate (1.44 g, 13.5 mmol) in benzene and 3 ml of water was purged with nitrogen for 30 mins. Tetrakis(triphenylphosphine)-palladium(0) (264 mgs, 0.2 mmol) was added to the mixture and was heated to 75° C. overnight. The reaction mixture was partitioned between ethyl acetate and water. Organic layer was separated and washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a brown solid which was recrystallized to give 1 g (yield, 80%) of white solid. The product gave satisfactory NMR.

Workup

  1. customwas purged with nitrogen for 30 mins
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. customOrganic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a brown solid which
  9. customwas recrystallized
  10. customto give
  11. custom1 g (yield, 80%) of white solid
  12. customThe product gave satisfactory NMR

Sources & evidence

ORD record
ord-c905db6a9fd843aab51919be790f74e8
Source dataset
uspto-grants-2006_01
Patent number
US06989382B2

Reaction notes

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