Cyclohexane → HCID 86629326, compound

HRID 549919Notes

Reaction equation

HRID 549919 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/I)=[CH:9]/[CH2:10][O:11][C:12]2[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:14]([CH3:24])[CH:13]=2)=[CH:4][CH:3]=1.[S:26]1[C:30]([Sn](CCCC)(CCCC)CCCC)=[CH:29][C:28]2[CH:44]=[CH:45][CH:46]=[CH:47][C:27]1=2.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C1CCCCC1>CN(C)C=O>[S:26]1[C:30](/[C:8](/[C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:9]\[CH2:10][O:11][C:12]2[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:14]([CH3:24])[CH:13]=2)=[CH:29][C:28]2[CH:44]=[CH:45][CH:46]=[CH:47][C:27]1=2

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2735461(1-Benzothiophen-2-yl)tributylstannaneHCID 86620182Methyl (Z)-[4-[3-(4-Bromophenyl)-3-iodoallyloxy]-2-methylphenoxy]acetate

Product 1

HCID 86629326HCID 86629326, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Methyl (Z)-[4-[3-(4-bromophenyl)-3-iodoallyloxy]-2-methylphenoxy]acetate (760 mg, 1.47 mmol) and (benzo[b]thiophen-2-yl)-tributyltin (0.72 g, 1.7 mmol) were dissolved in anhydrous N,N-dimethylformamide (20 mL) and the solution was degassed. 0.15 M solution of tri-t-butylphosphine in cyclohexane (1.2 mL, 0.18 mmol) and tris(dibenzylidenacetone)dipalladium chloroform complex (46 mg, 0.044 mmol) were added; the reaction solution was degassed again and then stirred under inert atmosphere at 50° C. for 2 h. The reaction mixture was diluted with ethyl acetate (50 mL) and extracted with 10% aqueous solution of potassium fluoride (50 mL), water (2×50 mL) and brine (2×30 mL). The organic layer was dried with anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 95:5-90:10) yielding methyl (Z)-[4-[3-(benzo[b]thiophen-2-yl)-3-(4-bromophenyl)allyloxy]-2-methylphenoxy]-acetate.

Workup

  1. customthe solution was degassed
  2. customthe reaction solution was degassed again
  3. additionThe reaction mixture was diluted with ethyl acetate (50 mL)
  4. extractionextracted with 10% aqueous solution of potassium fluoride (50 mL), water (2×50 mL) and brine (2×30 mL)
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 95:5-90:10)

Sources & evidence

ORD record
ord-08fe598f8516498e916dd9f4d4f4882c
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Reaction notes

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