Potassium Carbonate → Methyl 3-methyl-4-(4-methyl-3-thienyl)benzoate

HRID 1950809Notes

Reaction equation

HRID 1950809 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[CH3:13][C:14]1[C:15](B(O)O)=[CH:16][S:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.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>[CH3:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[C:15]1[C:14]([CH3:13])=[CH:18][S:17][CH:16]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 3294148Methyl 4-bromo-3-methylbenzoateHCID 50839314-Methyl-3-thiopheneboronic acid

Product 1

HCID 58438818Methyl 3-methyl-4-(4-methyl-3-thienyl)benzoateYield 92%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A suspension of methyl 4-bromo-3-methylbenzoate (ABCR AV19078; 3 g; 13.10 mmol; 1 eq.), 4-methyl-3-thiopheneboronic acid (Aldrich 542393; 2.05 g; 14.41 mmol; 1.10 eq.), potassium carbonate (9.05 g; 65.48 mmol; 5 eq.) and tetrakis(triphenylphosphine)palladium(0) (1.51 g; 1.31 mmol; 0.10 eq.) in toluene (15 mL) and water (15 mL) was refluxed for 3 hours. The resulting mixture was filtered through a short pad of Celite, which was further washed with toluene. After evaporation of the solvent, the residue taken up in ethyl acetate and washed successively with sat. aq. NaHCO3, water and brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (2.96 g, 92%) as a brown oil.

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationThe resulting mixture was filtered through a short pad of Celite, which
  3. washwas further washed with toluene
  4. customAfter evaporation of the solvent
  5. washwashed successively with sat. aq. NaHCO3, water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-709490f274c54d65b4a793914e51d1e2
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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