((4-Bromobutoxy)methyl)benzene → [(Heptyloxy)methyl]benzene

HRID 2304111Notes

Reaction equation

HRID 2304111 reaction equation
[Mg].BrCCCCOCC1C=CC=CC=1.[Cu](C#N)C#N.F[C:21]1[CH:26]=[CH:25][C:24]([CH:27]([O:31][CH:32]([C:36]2[CH:41]=[CH:40][C:39](F)=[CH:38][CH:37]=2)C2OC2)C2OC2)=[CH:23][CH:22]=1>C1COCC1.C(OCC)(=O)C.CCCCCC>[CH2:27]([O:31][CH2:32][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:24]1[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 4422181((4-Bromobutoxy)methyl)benzeneHCID 5462224MagnesiumHCID 57037655p-Fluorophenylglycidyl etherHCID 178418260HCID 178418260, compound

Product 1

HCID 285096[(Heptyloxy)methyl]benzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Magnesium (2.4 g, 98 mmol) was added to a 250 ml flask and flame dried. Dry THF, 25 ml, and 1 ml of dibromoethane were then added. 1-Bromo-4-benzyloxy-butane 41 (12 g, 49.4 mmol) dissolved in 50 ml of dry THF was added dropwise and the reaction mixture was stirred at room temperature. After 1 hour, the reaction mixture is cooled in an ice-water bath and 90 mg of copper cyanide is added. After 10 minutes in an ice-bath, 4-fluorophenyl-glycidyl ether (5 g, 29.6 mmol) dissolved in 30 ml of dry THF is added slowly. The reaction is monitored by TLC (ethyl acetate:hexane 3:7). After 15 minutes, the reaction is quenched with saturated aqueous ammonium chloride, concentrated and partitioned between water-ethyl acetate. The ethyl acetate layer is then washed with brine, dried over Na2SO4 and concentrated to give the desired benzyloxy-heptane 42. The structure was confirmed by 1H-NMR.

Workup

  1. temperatureflame
  2. customdried
  3. additionDry THF, 25 ml, and 1 ml of dibromoethane were then added
  4. additionwas added dropwise
  5. temperaturethe reaction mixture is cooled in an ice-water bath
  6. waitAfter 10 minutes in an ice-bath
  7. additionis added slowly
  8. waitAfter 15 minutes
  9. customthe reaction is quenched with saturated aqueous ammonium chloride
  10. concentrationconcentrated
  11. custompartitioned between water-ethyl acetate
  12. washThe ethyl acetate layer is then washed with brine
  13. dry with materialdried over Na2SO4
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-246c6cd2426b47d3aa995f1de32a8899
Source dataset
uspto-grants-2002_08
Patent number
US06433197B1

Reaction notes

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