Potassium Carbonate → HCID 86643105, compound

HRID 1099377Notes

Reaction equation

HRID 1099377 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:13]=[O:14])[C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[C:10]=1[O:11][CH3:12].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.[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>[CH3:12][O:11][C:10]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5]=2[C:4]([CH:13]=[O:14])=[CH:3][C:2]=1[C:20]1[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 86643106HCID 86643106, compound

Product 1

HCID 86643105HCID 86643105, compoundYield 22.7%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
87.5 °C

Procedure

To a suspension of 6-Bromo-7-methoxy-indan-4-carbaldehyde (0.2 gm, 0.00078 mole), 4-Methoxyphenyl boronic acid (0.122 gm, 0.0008 mole) and Potassium carbonate (0.27 gm, 0.0019 mole) in Toluene (5 ml) and water (5 ml), Tetrakis (triphenylphosphine) palladium(0) (2 mg) was and heated to 85-90° C. and stirred for 6 hrs. Toluene was distilled off and the obtained residue was dissolved in Diethyl ether (50 ml). Further it was washed with water (20 ml) and ether was distilled under vacuum to give a crude mass which was purified by column chromatography using Ethyl acetate:Hexane (1:99) as a mobile phase. The fractions were distilled to give 50 mg of desired product as a solid.

Workup

  1. distillationToluene was distilled off
  2. dissolutionthe obtained residue was dissolved in Diethyl ether (50 ml)
  3. washFurther it was washed with water (20 ml) and ether
  4. distillationwas distilled under vacuum
  5. customto give a crude mass which
  6. customwas purified by column chromatography
  7. distillationThe fractions were distilled

Sources & evidence

ORD record
ord-01a573ccfe1c4ea69f293a4c27431119
Source dataset
uspto-grants-2012_03
Patent number
US08143424B2

Reaction notes

Loading…