Sodium Carbonate → 6-(4-Chlorophenyl)benzo[d][1,3]dioxole-5-carbaldehyde

HRID 624373Notes

Reaction equation

HRID 624373 reaction equation
Br[C:2]1[C:3]([CH:11]=[O:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CO.CCOCC.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>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[C:3]([CH:11]=[O:12])=[CH:4][C:5]3[O:9][CH2:8][O:7][C:6]=3[CH:10]=2)=[CH:16][CH:15]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 950621,3-Benzodioxole-5-carboxaldehyde, 6-bromo-

Product 1

HCID 866428736-(4-Chlorophenyl)benzo[d][1,3]dioxole-5-carbaldehyde

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 6-bromobenzo[d][1,3]dioxole-5-carbaldehyde (4.6 g), 4-chlorophenylboronic acid (3.78 g) and tetrakis(triphenylphosphine)palladium(0) (0.232 g) in toluene (80 mL) and methanol (30 mL) was added 2N aqueous Na2CO3 (30 mL). The mixture was stirred at reflux overnight. The mixture was diluted with ether (400 mL) and washed with water, brine and dried over Na2SO4. After filtration and concentration of the solvent, the residue was loaded on a column and eluted with 3% ethyl acetate in hexane to give the product.

Workup

  1. temperatureat reflux overnight
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration of the solvent
  5. washeluted with 3% ethyl acetate in hexane
  6. customto give the product

Sources & evidence

ORD record
ord-7249493d16b04d209be8c49e3d2a5f49
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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