Dichloromethane → Ethyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-methoxy-benzoate

HRID 2177710Notes

Reaction equation

HRID 2177710 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:25]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26]1.C(Cl)Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH3:23])[C:14]([C:27]3[CH:28]=[CH:29][O:25][CH:26]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 2734358Furan-3-boronic acidHCID 67107394Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate2×

Product 1

HCID 67107652Ethyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-methoxy-benzoateYield 63.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 61, 0.13 g), furan-3-yl boronic acid (0.036 g), palladium chloride dppf adduct with DCM (0.026 g) and cesium carbonate (0.3 g) in THF (3.5 ml) and water (0.5 ml) was sealed in a microwave vial and degassed. The mixture was then heated in the microwave at 140° C. for 10 minutes. After cooling, the mixture was poured into water and extracted with ethyl acetate. The organic phase was dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60% to give ethyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-methoxy-benzoate (0.08 g) as a colourless gum.

Workup

  1. customwas sealed in a microwave vial and
  2. customdegassed
  3. temperatureAfter cooling
  4. additionthe mixture was poured into water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by chromatography on silica
  10. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60%

Sources & evidence

ORD record
ord-407be453a39246a0b9d20a1d917a05d1
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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