Iodine → HCID 22408140, compound

HRID 1654726Notes

Reaction equation

HRID 1654726 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[CH:7][C:6]=1[CH3:20].[CH3:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=[O:26].[Cl-].[NH4+]>O1CCCC1>[Si:13]([O:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([CH:25]([OH:26])[C:24]2[CH:27]=[CH:28][CH:29]=[C:22]([CH3:21])[CH:23]=2)=[C:6]([CH3:20])[CH:7]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

7

Reactant 5

HCID 807IodineHCID 121053-MethylbenzaldehydeHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 22408124HCID 22408124, compound

Product 1

HCID 22408140HCID 22408140, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Magnesium (0.84 g, 34.6 millimol) was suspended in tetrahydrofuran (30 ml), and thereto was added a small amount of iodine. Under nitrogen atmosphere, a solution of 2-bromo-5-t-butyldimethylsilyloxymethyltoluene (10 g, 31.6 millimol) in tetrahydrofuran (10 ml) was added. When the mixture was heated for some time, the reaction was started, and heat generated. After stirring for 2 hours as it was, m-methylbenzaldehyde (3.16 g, 26.3 millimol) was added. After stirring for 2 hours, to the mixture was added saturated aqueous ammonium chloride solution, 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=1:6) to give the title compound (6 g, 16.8 millimol, 64%).

Workup

  1. temperatureWhen the mixture was heated for some time
  2. temperatureheat
  3. stirringAfter stirring for 2 hours, to the mixture
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customThe residue was separated
  9. custompurified

Sources & evidence

ORD record
ord-09129e1bf3224287a14b47b2c3bd50ac
Source dataset
uspto-grants-1995_04
Patent number
US05409928

Reaction notes

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