Tetrahydrofuran → 2-Fluoro-4(2,2,4,4-tetramethyl-chroman-6yl-ethynyl)-benzoic acid methyl ester

HRID 51657Notes

Reaction equation

HRID 51657 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[CH2:7][C:6]2([CH3:16])[CH3:15])#[CH:2].[CH3:17][O:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][C:21]=1[F:27].C(N(CC)CC)C.O1CCCC1>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.C(OCC)(=O)C>[CH3:17][O:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([C:2]#[C:1][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[O:9][C:8]([CH3:14])([CH3:13])[CH2:7][C:6]3([CH3:16])[CH3:15])=[CH:22][C:21]=1[F:27]

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 156611382,2,4,4-Tetramethyl-6-ethynylchromanHCID 22568800Methyl 2-fluoro-4-iodobenzoate2×

Product 1

HCID 695488832-Fluoro-4(2,2,4,4-tetramethyl-chroman-6yl-ethynyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure F and using 6-ethynyl-2,2,4,4-tetramethylchroman (0.11 g, 0.51 mmol), methyl-2-fluoro-4-iodo-benzoate (Reagent G, 0.14 g, 0.51 mmol), triethyl amine (5 mL), tetrahydrofuran(10 mL), copper(I)iodide(0.030 g, 0.16 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.110 g, 0.16 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-10% ethyl acetate in hexane as the eluent, the title compound was obtained (0.14 g, 79%).

Sources & evidence

ORD record
ord-06942b89534c44edbd7d63cf3f6313d9
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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