Trifluoroacetic acid → HCID 57586461, compound

HRID 420405Notes

Reaction equation

HRID 420405 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[C:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[CH:25])=[CH:17][CH:16]=[CH:15][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])([OH:3])=[O:2].[Br:26][C:27]1[CH:28]=[C:29](I)[CH:30]=[C:31]([Br:33])[CH:32]=1.C(O)(C(F)(F)F)=O>C1COCC1.CCN(CC)CC.[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:1]([CH2:4][CH2:5][C:6]1[C:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[C:25][C:29]2[CH:28]=[C:27]([Br:26])[CH:32]=[C:31]([Br:33])[CH:30]=2)=[CH:17][CH:16]=[CH:15][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])([OH:3])=[O:2]

Participants

8

Reactant 3

HCID 6422Trifluoroacetic acidHCID 110684371,3-DIBROMO-5-IODOBENZENEHCID 57586440HCID 57586440, compound

Product 1

HCID 57586461HCID 57586461, compoundYield 60%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[2-(2-Carboxy-ethyl)-3-hept-6-ynyl-phenoxy]-butyric acid (250 mg, 0.72 mmol), 3,5-dibromoiodobenzene (preparation in J. Org. Chem. 2003, 68, 8750) (261 mg, 0.72 mmol), CuI (7 mg, 0.036 mmol) in THF (5 mL) and Et3N (5 mL) was added bis-(triphenylphosphine)palladium(II) dichloride (25 mg, 0.036 mmol). The reaction mixture was heated at 60° C. for 3 h. Then the reaction mixture was cooled down, a few drop of TFA was added and the resulting mixture was evaporated under vacuo. The crude material was purified by column chromatography using a gradient from EtOAc to 20% MeOH-EtOAc as eluant to give the title compound (240 mg, 60%) as a oil. HR-MS-EI(+): calculated for C26H28O5Br2(M+Na) 601.0195, found 601.0193.

Workup

  1. temperatureThen the reaction mixture was cooled down
  2. customthe resulting mixture was evaporated under vacuo
  3. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-37b2d7fae55d4c39bc3118eae686a320
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

Loading…