Ethyl Acetate → HCID 85891901, compound

HRID 971141Notes

Reaction equation

HRID 971141 reaction equation
Br[CH2:2][C:3]1([C:6]2[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=2)[CH2:5][CH2:4]1.[N-:13]=[N+:14]=[N-:15].[Na+].CCOC(C)=O>CN(C=O)C>[N:13]([CH2:2][C:3]1([C:6]2[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=2)[CH2:5][CH2:4]1)=[N+:14]=[N-:15]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 69516060HCID 69516060, compound

Product 1

HCID 85891901HCID 85891901, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part A. 1-(1-Bromomethylcyclopropyl)-4-iodobenzene (2.0 g, 5.97 mmol) and NaN3 (1.0 g, 15.38 mmol, 2.6 eq) were stirred in DMF (10 mL) overnight. Analytical LC-MS showed completion of the reaction. EtOAc was added to the solution. The mixture was washed with H2O and brine, dried over MgSO4, and concentrated to give 1-(1-azidomethyl-cyclopropyl)-4-iodobenzene (1.43 g, yield: 80%). The azide (1.40 g, 4.68 mmol) and PPh3 (1.84 g, 7.02 mmol, 1.5 eq) were stirred in THF (10 mL) at RT for 40 min. H2O (2 mL) was added, and the solution was stirred at 50° C. for 6 h. LC-MS showed completion of the reaction. The mixture was extracted with Et2O (2×). The aqueous layer was basified with 50% NaOH, extracted with CH2Cl2 (2×), washed with H2O, brine, dried over MgSO4, and concentrated to give 1-(4-iodophenyl)cyclopropyl methylamine (0.98 g, yield: 75%).

Workup

  1. customcompletion of the reaction
  2. washThe mixture was washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3b2d3da4434b4793a5b84f1b54408db2
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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