Potassium Carbonate → HCID 86599129, compound

HRID 2116019Notes

Reaction equation

HRID 2116019 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[CH:18]=[CH:19][CH:20]=[C:21](Br)[C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:23]1(/[CH:29]=[CH:30]/B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>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[CH:18]=[CH:19][CH:20]=[C:21](/[CH:30]=[CH:29]/[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5702628Styrylboronic acidHCID 58747572(7-Bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86599129HCID 86599129, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 178424406HCID 178424406, compoundCatalyst

Procedure

Treatment of (±)-(7-bromo-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (8.0 g, 20.9 mmol) with trans-2-phenylvinylboronic acid (4.63 g, 31.3 mmol), dichlorobis(tri-o-tolylphosphine)-palladium(II) (0.82 g, 1.04 mmol), and potassium carbonate (7.21 g, 52.2 mmol) generally according to the procedure described for Intermediate 37 provided 6.59 g (78%) of (±)-{7-[(E)-2-phenylvinyl]-2,3-dihydro-1-benzofuran-2-yl}methyl 4-methylbenzenesulfonate as a light yellow solid. mp 120-122° C.; Anal. calcd. for C24H22O4S: C, 70.91; H, 5.45. Found: C, 70.78; H, 5.56.

Sources & evidence

ORD record
ord-50c7d1813a1c439fb4b75e6f707f926d
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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