(1-Bromoethyl)benzene → (1-Phenylethyl)hydrazine

HRID 271833Notes

Reaction equation

HRID 271833 reaction equation
Br[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].O.[NH2:11][NH2:12]>C1COCC1>[C:4]1([CH:2]([NH:11][NH2:12])[CH3:3])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 11454(1-Bromoethyl)benzeneHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 6179(1-Phenylethyl)hydrazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-bromoethylbenzene Compound 3a (8.0 mL, 58.0 mMol) was added to a solution of hydrazine hydrate Compound 3b (20 mL) in THF (80 mL) which was then heated to reflux for 8 hrs. The solvent was removed in vacito and Et2O (100 mL) was added. The organic layer was washed with brine, separated and dried over Na2SO4. The solvent was removed in vacuo to yield (1-phenyl-ethyl)-hydrazine Compound 3c as a pale yellow oil (5.8 g), used in the next step without purification. MS m/z 137 (M+H, 70%), 105 (M-NHNH2, 100%).

Workup

  1. temperaturewas then heated
  2. temperatureto reflux for 8 hrs
  3. customThe solvent was removed in vacito and Et2O (100 mL)
  4. additionwas added
  5. washThe organic layer was washed with brine
  6. customseparated
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-dff855dc5c61455bbf8bdfa9ab6bf477
Source dataset
uspto-grants-2008_11
Patent number
US07452997B2

Reaction notes

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