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

HRID 844653Notes

Reaction equation

HRID 844653 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;, 0.5 1 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-eee13b0f1efe43d1990e4c09c694f1ab
Source dataset
uspto-grants-2002_04
Patent number
US06380256B1

Reaction notes

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