Tetrahydrofuran → 4-(3,5-Di-tert-butyl-4-methoxy-phenylethynyl)-2-fluoro-phenyl-acetic acid methyl ester

HRID 1936187Notes

Reaction equation

HRID 1936187 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]#[CH:12])[CH:8]=[C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:6]=1[O:17][CH3:18])([CH3:4])([CH3:3])[CH3:2].C(O[C:23]1[CH:28]=[CH:27][C:26](I)=[C:25]([CH3:30])[C:24]=1[F:31])(=O)C.C(N(CC)CC)C.O1CCCC1.[C:44]([O:47][CH2:48]C)(=[O:46])C>CCCCCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:48][O:47][C:44](=[O:46])[CH2:30][C:25]1[CH:26]=[CH:27][C:28]([C:12]#[C:11][C:9]2[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]([O:17][CH3:18])=[C:7]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=2)=[CH:23][C:24]=1[F:31]

Participants

9

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 225688511,3-Di-tert-butyl-5-ethynyl-2-methoxy-benzene2×HCID 69548383Methyl-2-fluoro-4-iodo-phenyl acetate

Product 1

HCID 695488624-(3,5-Di-tert-butyl-4-methoxy-phenylethynyl)-2-fluoro-phenyl-acetic acid methyl esterYield 89%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolvent

Procedure

Following General Procedure F and using 1,3-di-tert-butyl-5-ethynyl-2-methoxy-benzene (Intermediate 169, 0.087 g, 0.33 mmol), methyl-2-fluoro-4-iodo phenyl acetate (Reagent H, 0.088 g, 0.30 mmol), triethyl amine (5 mL), anhydrous tetrahydrofuran (10 mL), copper(I)iodide (0.02 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.06 g, 0.085 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent, the title compound (0.122 g, 89%) was obtained.

Sources & evidence

ORD record
ord-1d73bea45fb94952af3c372788a9f3ee
Source dataset
uspto-grants-2002_05
Patent number
US06387951B1

Reaction notes

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