Iodine → HCID 22408234, compound

HRID 1654736Notes

Reaction equation

HRID 1654736 reaction equation
[CH2:1]1[O:12][CH:4]([C:5]2[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=2)[O:3][CH2:2]1.[Mg].II.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:33]=[CH:34][CH:35]=1)[CH2:21]C1C=C(C)C=CC=1S([O-])(=O)=O.[Cl-].[NH4+]>O1CCCC1.C1C=CC=CC=1.[Cu+]>[CH2:1]1[O:12][CH:4]([C:5]2[CH:10]=[CH:9][C:8]([CH2:21][C:20]3[CH:33]=[CH:34][CH:35]=[C:18]([O:17][CH3:16])[CH:19]=3)=[CH:7][CH:6]=2)[O:3][CH2:2]1

Participants

9

Reactant 5

HCID 807IodineHCID 25517Ammonium ChlorideHCID 27738422-(4-Bromophenyl)-1,3-dioxolaneHCID 5462224Magnesium2×HCID 22408181HCID 22408181, compound

Product 1

HCID 22408234HCID 22408234, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 104815Copper(1+)CatalystHCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromobenzaldehyde ethylene acetal (1.5 g, 6.5 millimol) in tetrahydrofuran (7 ml) were added magnesium (170 mg, 7 millimol) and a small amount of iodine, and the mixture was vigorously stirred under nitrogen atmosphere. After most of magnesium was dissolved, the solution was added to a solution of 3-methoxybenzyltosylate(1.46 g, 5 millimol) and copper(I) bromidedimethylsulfide complex (50 mg, 0.25 millimol) in benzene (14 ml). The mixture was stirred at room temperature for 22 hours. Next, saturated ammonium chloride solution was added, and the mixture was extracted with ethyl acetate, the organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure, The residue was separated and purified by using a silica-gel column chromatography (ethyl acetate:n-hexane=1:3) to give the title compound (850 mg, 3.14 millimol, 63%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe residue was separated
  6. custompurified

Sources & evidence

ORD record
ord-0309f9b9ca224dd986dcb0362292bdc1
Source dataset
uspto-grants-1995_04
Patent number
US05409928

Reaction notes

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