Potassium Carbonate → (+/-)-(4-Phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate

HRID 2115931Notes

Reaction equation

HRID 2115931 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH2:17][C:16]3[C:18](Br)=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(OCC)C.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH2:17][C:16]3[C:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 86599073(+/-)-(4-Bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86599074(+/-)-(4-Phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateYield 73.2%

Reagents, catalysts & solvents 3

HCID 178424406HCID 178424406, compoundCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (±)-(4-bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (2.05 g, 5.21 mmol) and phenylboronic acid (0.952 g, 7.81 mmol) in dioxane (50 mL) heated to 100° C. was added dichlorobis(tri-o-tolylphosphine)-palladium(II) (0.205 g, 0.261 mmol) and potassium carbonate (1.80 g, 13.04 mmol) and the reaction mixture was allowed to stir at 100° C. for 12 h. The reaction mixture was cooled to room temperature, diluted with diethyl ether (250 mL), and filtered (celite). The organic layer was washed with water (2×100 mL) and saturated aqueous sodium chloride (100 mL), was dried (magnesium sulfate), and the solvent was removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:9) provided 1.45 g (73%) of (±)-(4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a clear oil. Rf=0.34 (silica, ethyl acetate:hexanes 1:4); Anal. calcd. for C22H20O4S: C, 69.45; H, 5.30. Found: C, 69.17; H, 5.30.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered (celite)
  3. washThe organic layer was washed with water (2×100 mL) and saturated aqueous sodium chloride (100 mL)
  4. dry with materialwas dried (magnesium sulfate)
  5. customthe solvent was removed in vacuo
  6. customto provide a crude oil
  7. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 1:9)

Sources & evidence

ORD record
ord-ad9924e471d444fda333b0896e3b3b4d
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

Loading…