Ethyl 2-fluoro-4-iodobenzoate → HCID 21846688, compound

HRID 619655Notes

Reaction equation

HRID 619655 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=[O:15])#[CH:2].[F:16][C:17]1[CH:27]=[C:26](I)[CH:25]=[CH:24][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CCN(CC)CC.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.[Cu]I>[F:16][C:17]1[CH:27]=[C:26]([C:2]#[C:1][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[O:9][C:8]([CH3:13])([CH3:14])[CH2:7][C:6]3=[O:15])[CH:25]=[CH:24][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 2

HCID 18761561Ethyl 2-fluoro-4-iodobenzoateHCID 21846681HCID 21846681, compound2×

Product 1

HCID 21846688HCID 21846688, compoundYield 72.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 6-ethynyl-2,2-dimethylchroman-4-one (Compound 262, 314.0 mg, 1.57 mmol) and ethyl 2-fluoro-4-iodobenzoate (440.0 mg, 1.50 mmol) in 10.0 mL Et3N was purged with argon for 15 minutes. To this solution was added bis(triphenylphosphine)-palladium(II) chloride (275.0 mg, 0.39 mmol) and copper(I) iodide (75.0 mg, 0.39 mmol). After sparging for an additional 10 minutes with argon, the solution was stirred overnight at room temperature. The reaction mixture was filtered through a pad of Celite using an Et2O wash. Concentration of the filtrate under reduced pressure, followed by column chromatography (3-5% EtOAc-hexanes) of the residual solid afforded 400.0 mg (69%) the title compound as an orange solid. 1H NMR (300 MHz, CDCl3) δ: 8.05 (1H, d, J=2.1 Hz), 7.90 (1H, d, J=7.8 Hz), 7.60 (1H, dd, J=2.2 8.5 Hz), 7.29 (1H, dd, J=1.5, 8.2 Hz), 7.25 (1H, d, J=11.4 Hz), 6.93 (1H, d, J=8.5 Hz), 4.39 (2H, q, J=7.1 Hz), 2.75 (2H, s), 1.48 (6H, s), 1.40 (3H, t, J=7.1 Hz).

Workup

  1. customAfter sparging for an additional 10 minutes with argon
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. washwash

Sources & evidence

ORD record
ord-7ed4ff2f9c1e41f4a28c001613e8721c
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

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