Iodine → HCID 22131264, compound

HRID 1857561Notes

Reaction equation

HRID 1857561 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[O:13][CH3:14].CO[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[O:24][CH2:25][C:26]([CH3:29])([CH3:28])[N:27]=1.[Cl-].[NH4+]>C1COCC1>[CH3:28][C:26]1([CH3:29])[CH2:25][O:24][C:23]([C:18]2[CH:17]=[CH:22][CH:21]=[CH:20][C:19]=2[C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=2[O:13][CH3:14])=[N:27]1

Participants

7

Reactant 5

HCID 807IodineHCID 25517Ammonium ChlorideHCID 872661-Bromo-2,4-dimethoxybenzeneHCID 3331894,4-Dimethyl-2-(2-methoxyphenyl)oxazolineHCID 5462224Magnesium

Product 1

HCID 22131264HCID 22131264, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of magnesium powder (409 mg, 16.8 mmol) in THF (10 ml) containing a few crystals of iodine was heated whilst a solution of 1-bromo-2,4-dimethoxybenzene (3.65 g, 16.8 mmol) in THF (20 ml) was added dropwise over 20 minutes. After completion of the addition, the mixture was refluxed for 1.25 hours and then allowed to cool to room temperature. The Grignard solution was transferred via syringe to a solution of 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (J. Org. Chem., 1978, 43, 1372, 2.50 g, 12.9 mmol) in THF (10 ml) at room temperature and the mixture was stirred at room temperature for 42 hours. Saturated ammonium chloride solution was added and the product was extracted into diethyl ether. The extracts were dried (K2CO3) and concentrated. Purification by column chromatography on silica gel (elution with 40-60% ethyl acetate in iso-hexane) gave the title compound as a viscous oil. Yield 4.029 g (84%).

Workup

  1. additionwas added dropwise over 20 minutes
  2. additionAfter completion of the addition
  3. temperaturethe mixture was refluxed for 1.25 hours
  4. extractionthe product was extracted into diethyl ether
  5. dry with materialThe extracts were dried (K2CO3)
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (elution with 40-60% ethyl acetate in iso-hexane)

Sources & evidence

ORD record
ord-4b44dedc6b9e4bbdb054cc0c49c14926
Source dataset
uspto-grants-2000_11
Patent number
US06147111

Reaction notes

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