Dimethylformamide → HCID 57571708, compound

HRID 2097474Notes

Reaction equation

HRID 2097474 reaction equation
CN(C)C=O.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][O:15][CH3:16])[C:8]=1[OH:17].C(=O)([O-])[O-].[K+].[K+].[CH:24]1([CH2:27]Br)[CH2:26][CH2:25]1>O>[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][O:15][CH3:16])[C:8]=1[O:17][CH2:27][CH:24]1[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 57571705HCID 57571705, compound

Product 1

HCID 57571708HCID 57571708, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To 200 ml of N,N-dimethylformamide solution containing 23.3 g (0.10 mol) of 2-bromo-6-methoxymethoxyphenol (see Synthesis, 2001, 741-744) were added 13.8 g (0.10 mol) of potassium carbonate and 19.5 ml (0.20 mol) of cyclopropylmethyl bromide, and the mixture was stirred at 80° C. for 2 hours. After completion of the reaction, water was added to the reaction mixture, and extracted with toluene. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=9:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 24.1 g of the title compound as a colorless oil. (Yield: 84%)

Workup

  1. additionwas added to the reaction mixture
  2. extractionextracted with toluene
  3. customThe organic layer after separation
  4. washwas washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionthe fractions containing the desired compound
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-3d5ad72cee024fbf9d840d2be9d3bf15
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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