Sodium Carbonate → HCID 70011311, compound

HRID 1369058Notes

Reaction equation

HRID 1369058 reaction equation
[C:1]([O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1Br)([CH3:4])([CH3:3])[CH3:2].B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].Br[C:40]1[CH:49]=[CH:48][CH:47]=[CH:46][C:41]=1[C:42]([O:44][CH3:45])=[O:43].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C=O)C>[CH3:45][O:44][C:42]([C:41]1[C:40]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:15])=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:43]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 11894Methyl 2-bromobenzoateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 14371760tert-butyl 2-(2-bromophenyl)acetate

Product 1

HCID 70011311HCID 70011311, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2-bromo-phenyl)-acetic acid tert-butyl ester (678 mg, 2.5 mmol), bis(pinacolato)diboron (698 mg, 2.75 mmol), potassium acetate (736 mg, 7.5 mmol) and DMF (15 mL) was added PdCl2(dppf) (61 mg, 0.75 mmol). After evacuating and refilling with nitrogen three times, the reaction was heated to 80° C. for 2 h. After cooling to room temperature, methyl 2-bromo-benzoate (1.08 g, 5.0 mmol), 2M Na2CO3 aqueous (6.25 mL) and PdCl2(dppf) (61 mg, 0.75 mmol) was added to the reaction.). After evacuating and refilling with nitrogen three times again, the reaction was heated to 80° C. for 14 h. After cooling to room temperature, the mixture was poured into water (15 mL) and extracted with ether (3×25 mL). The combined organic layers were washed with water (3×25 mL), brine, dried (magnesium sulfate), and concentrated. The title compound was isolated in 22% yield as an oil following chromatography on silica gel utilizing ethyl acetate/hexane as solvent.

Workup

  1. customAfter evacuating
  2. temperatureAfter cooling to room temperature
  3. customAfter evacuating
  4. temperaturethe reaction was heated to 80° C. for 14 h
  5. temperatureAfter cooling to room temperature
  6. additionthe mixture was poured into water (15 mL)
  7. extractionextracted with ether (3×25 mL)
  8. washThe combined organic layers were washed with water (3×25 mL), brine
  9. dry with materialdried (magnesium sulfate)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d176bb871f094ad88eef95dbc9487f13
Source dataset
uspto-grants-2003_06
Patent number
US06576632B1

Reaction notes

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