Potassium Phosphate, Tribasic → (+/-)-[7-(3,5-Dichlorophen yl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate

HRID 2115948Notes

Reaction equation

HRID 2115948 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](OS(C(F)(F)F)(=O)=O)[C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[C:35]([Cl:37])[CH:36]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[C:21]([C:33]4[CH:32]=[C:31]([Cl:30])[CH:36]=[C:35]([Cl:37])[CH:34]=4)[C:15]=3[O:14]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343313,5-Dichlorophenylboronic acidHCID 86599077(+/-)-(7-{[(Trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86599082(+/-)-[7-(3,5-Dichlorophen yl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonateYield 15%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Treatment of (±)-(7-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (1.5 g, 3.32 mmol) with 3,5-dichlorophenylboronic acid (0.95 g, 4.97 mmol), tetrakis(triphenylphosphine)palladium(0) (0.38 g, 0.33 mmol), and potassium phosphate (1.41 g, 6.64 mmol) generally according to the procedure described for Intermediate 50 provided 0.22 g (15%) of (±)-[7-(3,5-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate as a white solid. Rf=0.48 (silica, ethyl acetate:hexanes 1:3); mp 113-115° C.; Anal. calcd. for C22H18Cl2O4S: C, 58.8: H, 4.04. Found: C, 58.73; H, 3.77.

Sources & evidence

ORD record
ord-c9340748d09b486ab905c52a276ddc5b
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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