Sodium Bromide → Ethyl 6-benzenesulphonylmethyl-3-(furan-3-yl)-2-hydroxybenzoate

HRID 2177716Notes

Reaction equation

HRID 2177716 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]([OH:22])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:24]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25]1.O.[F-].[K+].[Br-].[Na+]>FC(F)(F)C1C=CC=CC=1.O1CCOCC1.[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>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([OH:22])[C:14]([C:26]3[CH:27]=[CH:28][O:24][CH:25]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 253881Sodium BromideHCID 2734358Furan-3-boronic acidHCID 23675105Potassium fluoride hydrateHCID 67108192Ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoate2×

Product 1

HCID 67107629Ethyl 6-benzenesulphonylmethyl-3-(furan-3-yl)-2-hydroxybenzoateYield 66.2%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 7368(Trifluoromethyl)benzeneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoate (Intermediate 52, 0.39 g), furan-3-yl boronic acid (0.16 g), potassium fluoride monohydrate (0.45 g), tetrakis-(triphenylphosphine) palladium (0.11 g), and sodium bromide (0.15 g) in α,α,α-trifluorotoluene (10 ml) and dioxane (2 ml) was degassed and heated in the microwave at 175° C. for 30 minutes. After cooling, the mixture was partitioned between ethyl acetate and water. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were dried (Na2SO4) 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 15-30% to give ethyl 6-benzenesulphonylmethyl-3-(furan-3-yl)-2-hydroxybenzoate (0.25 g) as a white solid.

Workup

  1. customwas degassed
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was further extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-30%

Sources & evidence

ORD record
ord-4a45f12542fd4752b1991aaef5358c6a
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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