Sodium Carbonate → HCID 18476029, compound

HRID 2187610Notes

Reaction equation

HRID 2187610 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.[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>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=2[CH3:21])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 821892-Bromo-4-nitrotolueneHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 18476029HCID 18476029, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Fluorophenylboronic acid (6.72 g; 0.048 mol) was added to a suspension of 2-bromo-4-nitrotoluene (6.9 g; 0.032 mol) and tetrakis(triphenylphosphine) palladium (1.5 g; 1.4 mmol) in DME (90 ml). After addition of aqueous sodium carbonate solution 2M (120 ml), the mixture was refluxed overnight. After extraction with ether and evaporation, the residue was purified by flash chromatography (ethyl acetate/petroleum ether 95/5 to give 2-(4-fluorophenyl)-4-nitrotoluene (6.66 g; 90%).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. extractionAfter extraction
  3. customwith ether and evaporation
  4. customthe residue was purified by flash chromatography (ethyl acetate/petroleum ether 95/5

Sources & evidence

ORD record
ord-b6c51f12605b4446aeee99ca681a37e8
Source dataset
uspto-grants-2002_06
Patent number
US06410539B1

Reaction notes

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