Sodium Carbonate → Ethyl 4-(3-chlorophenyl)furan-2-carboxylate

HRID 2190116Notes

Reaction equation

HRID 2190116 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[O:5][CH:6]=1.[Cl:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:3]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[O:5][CH:6]=2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 58064765Ethyl 4-bromofuran-2-carboxylate

Product 1

HCID 58064785Ethyl 4-(3-chlorophenyl)furan-2-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Under argon, 100 mg (0.46 mmol) of the compound from Example 3A are provided in 3 ml of 1,2-dimethoxyethane, and 107 mg (0.69 mmol) of 3-chlorophenylboronic acid, 2.4 ml (2.28 mmol) of an aqueous sodium carbonate solution (10%) and 32 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium(0) are added. Under microwave irradiation, the mixture is heated in a closed vessel at 80° C. for 15 min. The crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 81.0 mg (71% of theory) of the title compound are obtained.

Workup

  1. customUnder microwave irradiation
  2. customThe crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-3bb500a9187b4d61b9c9755dfe6956d3
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

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