Benzo(B)Thiophene-2-Boronic Acid → Methyl 4-benzo[b]thien-2-ylbenzoate

HRID 1096944Notes

Reaction equation

HRID 1096944 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[S:12]1[C:16](B(O)O)=[CH:15][C:14]2[CH:20]=[CH:21][CH:22]=[CH:23][C:13]1=2.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C.[Pd].O>[S:12]1[C:16]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=2)=[CH:15][C:14]2[CH:20]=[CH:21][CH:22]=[CH:23][C:13]1=2

Participants

7

Reactant 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 11430Potassium CarbonateHCID 12081Methyl 4-bromobenzoate

Product 1

HCID 4137384Methyl 4-benzo[b]thien-2-ylbenzoate

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 58759193palladium(I) acetateCatalystHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 4-bromobenzoate (430 mg, 2.00 mmol), 2-benzo[b]thiopheneboronic acid (392 mg, 2.20 mmol), palladium(0) acetate (2.2 mg, 0.010 mmol), potassium carbonate (691 mg, 5.00 mmol), tetrabutylammonium bromide (645 mg, 2.00 mmol) and water (2.2 mL) was stirred in a nitrogen atmosphere at 70° C. for 1 hour. Water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with sodium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography to obtain the title compound as a pale yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with aqueous saturated sodium chloride solution
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-8e9dcc039968418fba609e68a6da4c6f
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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