4-Iodophenol → Ethyl (2R)-4-(4'-hydroxybiphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanoate

HRID 533537Notes

Reaction equation

HRID 533537 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[CH3:15][C@@:16]([S:39]([CH3:42])(=[O:41])=[O:40])([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:25]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>[Pd+2].O1CCOCC1.O>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([C:27]2[CH:26]=[CH:25][C:24]([CH2:23][CH2:22][C@@:16]([CH3:15])([S:39]([CH3:42])(=[O:41])=[O:40])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:29][CH:28]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 66577950ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate

Product 1

HCID 66579462Ethyl (2R)-4-(4'-hydroxybiphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanoateYield 54%

Reagents, catalysts & solvents 2

HCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of palladium (II) EnCat (0.1 equiv), potassium carbonate (3.0 equiv), 4-iodophenol and ethyl(2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate, which may be prepared as in Preparation 8A, was heated to 80° C. in 10:1 1,4-dioxane-water to provide the title compound (54%) after purification by flash chromatography on silica gel. MS (LCMS) m/z 399.5 (M+Na). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.33 (t, J=7.13 Hz, 3H) 1.72 (s, 3H) 2.18-2.28 (m, 1H) 2.47-2.58 (m, 2H) 2.72-2.84 (m, 1H) 3.04 (s, 3H) 4.22-4.31 (m, 2H) 4.91 (s, 1H) 6.85-6.92 (m, 2H) 7.17-7.24 (m, 2H) 7.40-7.51 (m, 4H).

Sources & evidence

ORD record
ord-46e0039686aa4e5882feec86abbb9b47
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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