Sodium Bromide → HCID 67107366, compound

HRID 2177720Notes

Reaction equation

HRID 2177720 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[CH:20]=[CH:19][C:18](Br)=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:22]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23]1.O.[F-].[K+].[Br-].[Na+]>FC(F)(F)C1C=CC=CC=1.[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[CH:20]=[CH:19][C:18]([C:24]3[CH:25]=[CH:26][O:22][CH:23]=3)=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 253881Sodium BromideHCID 2734358Furan-3-boronic acidHCID 23675105Potassium fluoride hydrateHCID 67107956Methyl 2-benzenesulphonylmethyl-5-bromobenzoate2×

Product 1

HCID 67107366HCID 67107366, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 7368(Trifluoromethyl)benzeneSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of methyl 2-benzenesulphonylmethyl-5-bromobenzoate (Intermediate 63, 0.2 g), furan-3-yl boronic acid (0.091 g), tetrakis-(triphenylphosphine) palladium (0.063 g), potassium fluoride monohydrate (0.0.23 g) and sodium bromide (0.1 g) in α,α,α-trifluorotoluene (2.5 ml) was sealed in a microwave vial and the mixture was degassed then heated in the microwave at 175° C. for 30 minutes. After cooling, the mixture was diluted with DCM 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 0-40% to give methyl 2-(benzenesulphonylmethyl)-5-(furan-3-yl)benzoate (0.149 g) as a white solid.

Workup

  1. customwas sealed in a microwave vial
  2. customthe mixture was degassed
  3. temperatureAfter cooling
  4. additionthe mixture was diluted with DCM
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-40%

Sources & evidence

ORD record
ord-686344c624894881b47301bd101557a6
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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