Toluene → HCID 19093470, compound

HRID 487062Notes

Reaction equation

HRID 487062 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Cl[C:12]1[N:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[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.C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[N:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([O:16][CH3:17])=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 819931Methyl 2-chloronicotinateHCID 2734318(3-Bromophenyl)boronic acid

Product 1

HCID 19093470HCID 19093470, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4.02 g (20 mmole) of 3-bromophenyl boronic acid, 6.86 g (40 mmole) of methyl 2-chloronicotinate, 600 mg of tetrakis-(triphenylphosphine) palladium, 25 mL of 2M solution of sodium carbonate, 50 mL of toluene, and 13 mL of ethanol was heated 20 hours at 80°. The reaction mixture was cooled to r.t. and partitioned between ethyl acetate and saturated sodium chloride solution. The organic phase was washed with sodium chloride solution several times, and dried over anhydrous magnesium sulfate. Solvent removal gave a crude product, which was chromatographed on silica gel using 1:4 ethyl acetate:hexane mixture as eluant to give methyl 2-[3-bromophenyl]nicotinate as white amorphous powder.

Workup

  1. temperaturewas heated 20 hours at 80°
  2. custompartitioned between ethyl acetate and saturated sodium chloride solution
  3. washThe organic phase was washed with sodium chloride solution several times
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customSolvent removal
  6. customgave a crude product, which
  7. customwas chromatographed on silica gel using 1:4 ethyl acetate

Sources & evidence

ORD record
ord-fd57d6b251644c51b15b36f7e7e7f134
Source dataset
uspto-grants-1994_03
Patent number
US05294610

Reaction notes

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