Sodium Carbonate → HCID 18451490, compound

HRID 1270711Notes

Reaction equation

HRID 1270711 reaction equation
[F:1][C:2]1[C:8]([F:9])=[C:7](Br)[C:6]([F:11])=[C:5]([F:12])[C:3]=1[NH2:4].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.C(O)C>[F:1][C:2]1[C:8]([F:9])=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]([F:11])=[C:5]([F:12])[C:3]=1[NH2:4]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 6186714-Bromo-2,3,5,6-tetrafluoroaniline

Product 1

HCID 18451490HCID 18451490, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

2,3,5,6-Tetrafluoro-4-bromoaniline (13.8 g, 56.7 mmol) is dissolved in benzene (200 mL) and treated with 1.5 equivalents of phenylboronic acid (10.4 g, 85.1 mmol) and a catalytic amount of tetrakistriphenylphosphine palladium(0) (4.2 g, 3.6 mmol) as a solution in ethanol (30 mL). Sodium carbonate (60 mL of 2 M aqueous solution) is added and the reaction mixture stirred and heated to reflux temperature for 24 hours. After cooling to room temperature the mixture is partitioned between Et2O (500 mL) and water (250 mL). The organic layer is washed with brine, dried (MgSO4) and concentrated by rotary evaporator. The residual oil is purified by flash chromatography (9:1 hexanes/EtOAc) to give 2,3,5,6-tetrafluoro-4-phenylaniline as an oil.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 24 hours
  3. customis partitioned between Et2O (500 mL) and water (250 mL)
  4. washThe organic layer is washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated by rotary evaporator
  7. customThe residual oil is purified by flash chromatography (9:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-efd0175ca527483b827db0d3a68e28bf
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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