Iodine → HCID 23114134, compound

HRID 2376584Notes

Reaction equation

HRID 2376584 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:13])[CH3:12])=[CH:7][CH:6]=1.[CH:14]([C:16]1[C:24]2[O:23][C:22]([CH3:26])([CH3:25])[CH2:21][C:20]=2[C:19]([CH3:27])=[C:18]([NH:28][C:29](=[O:35])[CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:17]=1[CH3:36])=[O:15]>C1COCC1.O>[OH:15][CH:14]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:13])[CH3:12])=[CH:7][CH:6]=1)[C:16]1[C:24]2[O:23][C:22]([CH3:25])([CH3:26])[CH2:21][C:20]=2[C:19]([CH3:27])=[C:18]([NH:28][C:29](=[O:35])[CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:17]=1[CH3:36]

Participants

7

Reactant 4

HCID 807Iodine2×HCID 114621-Bromo-4-isopropylbenzeneHCID 5462224MagnesiumHCID 23113844HCID 23113844, compound

Product 1

HCID 23114134HCID 23114134, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of magnesium (198 mg, 8.13 mmol) and a catalytic amount of iodine was added dropwise under argon atmosphere a solution of 1-bromo-4-isopropylbenzene (1.62 g, 8.13 mmol) in THF (5 mL) under argon atmosphere at room temperature, and the reaction solution was heated until the color of iodine disappeared. To the reaction solution was added dropwise at room temperature a solution of N-(7-formyl-2,2,4,6-tetramethyl-2,3-dihydro-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide obtained in Example 340 (860 mg, 2.71 mmol) in THF (5 mL) and the mixture was stirred for 1 hour. Water was added to the reaction solution and the product was extracted with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure to synthesize 1.15 g (yield: 97%) of the title compound. Amorphous powder.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe combined organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-82a966c25e3242acb018213af2bbc485
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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