Sodium Bromide → Methyl 3-(2-acetylfuran-3-yl)-6-benzenesulfonylmethyl-2-hydroxybenzoate

HRID 1778358Notes

Reaction equation

HRID 1778358 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([OH:21])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([C:26]1[O:27][CH:28]=[CH:29][C:30]=1B(O)O)(=[O:25])[CH3:24].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:23]([C:26]1[O:27][CH:28]=[CH:29][C:30]=1[C:14]1[C:15]([OH:21])=[C:16]([C:11]([CH2:10][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[CH:12][CH:13]=1)[C:17]([O:19][CH3:20])=[O:18])(=[O:25])[CH3:24]

Participants

8

Reactant 4

HCID 253881Sodium BromideHCID 23423491(2-Acetylfuran-3-yl)boronic acidHCID 23675105Potassium fluoride hydrateHCID 66685467Methyl 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoate2×

Product 1

HCID 66685067Methyl 3-(2-acetylfuran-3-yl)-6-benzenesulfonylmethyl-2-hydroxybenzoateYield 48.8%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
175 °C

Procedure

A mixture of methyl 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoate (Intermediate 40, 0.4 g), 2-acetylfuran-3-boronic acid (0.24 g), tetrakis-(triphenylphosphine) palladium (0.12 g), potassium fluoride monohydrate (0.302 g) and sodium bromide (0.192 g) in α,α,α-trifluorotoluene (8 mL) and dioxane (4 mL) was degassed and then heated in the microwave at 175° C. for 30 minutes. The mixture was cooled and ethyl acetate and water were added. The organic layer was separated, washed with water, 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 10-25% to give methyl 3-(2-acetylfuran-3-yl)-6-(benzenesulfonylmethyl)-2-hydroxybenzoate (0.21 g) as a white solid.

Workup

  1. customwas degassed
  2. temperatureThe mixture was cooled
  3. additionethyl acetate and water were added
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (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 10-25%

Sources & evidence

ORD record
ord-e1cf22d6e7aa434bb9fb567e17005e2b
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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