3-Bromophenylhydrazine hydrochloride → 4-(3-Bromophenyhydrazono)-1-butanol

HRID 1955720Notes

Reaction equation

HRID 1955720 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[O:11]1[CH:15]=[CH:14][CH2:13][CH2:12]1>C1COCC1>[Br:2][C:3]1[CH:4]=[C:5]([NH:9][N:10]=[CH:15][CH2:14][CH2:13][CH2:12][OH:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 337573-Bromophenylhydrazine hydrochlorideHCID 709342,3-Dihydrofuran

Product 1

HCID 676131814-(3-Bromophenyhydrazono)-1-butanolYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under anhydrous conditions a solution of 3-bromophenylhydrazine hydrochloride (22.5 g, 100 mmol) and 2,3-dihydrofuran (7.55 ml, 100 mmol) in 200 ml of dry THF was stirred at ambient temperature for 3 h. The reaction mixture was partitioned between EtOAc and H2O. The organic phase was washed with H2O and brine. After drying (Na2 SO4), the solvent was evaporated to give 25.6 g of the product as a brown oil. The product was of suitable purity for use in the next step.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and H2O
  2. washThe organic phase was washed with H2O and brine
  3. customAfter drying (Na2 SO4)
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-82c84d912c254d23889f2da672dc0809
Source dataset
uspto-grants-1998_07
Patent number
US05776967

Reaction notes

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