Dimethylformamide → HCID 66760065, compound

HRID 1850420Notes

Reaction equation

HRID 1850420 reaction equation
Br[CH2:2][C:3]([CH3:5])=[CH2:4].CN(C=O)C.[Cl:11][C:12]1[C:13]([CH3:19])=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:4][C:3]([CH3:5])=[CH2:2])[C:13]=1[CH3:19]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 148563-Chloro-o-cresolHCID 3577853-Bromo-2-methyl-1-propene

Product 1

HCID 66760065HCID 66760065, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-bromo-2-methylpropene (8.5 mL, 84.2 mmol) was added to a mixture of DMF (200 mL) containing 3-chloro-2-methylphenol (10.0 g, 70.1 mmol) and potassium carbonate (19.4 g, 140 mmol), and the mixture was stirred at room temperature for 15 hours. The reaction solution was distributed using ethyl acetate and water, and the organic layer was washed with water and saturated saline, and then dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 10:1) to give 13.7 g of the title compound as an amorphous solid (yield: 99%).

Workup

  1. washthe organic layer was washed with water and saturated saline
  2. customdried
  3. customThe solvent was removed under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 10:1)

Sources & evidence

ORD record
ord-188bd3b0e06c4bc887ee5478518a4e95
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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