Boron trifluoride etherate → HCID 54537144, compound

HRID 728196Notes

Reaction equation

HRID 728196 reaction equation
C1C=C[NH+]=CC=1.[Br:7][Br-]Br.[CH2:10]([O:17][C:18]1[CH:19]=[C:20]([CH:27]=[CH:28][C:29](=[O:31])[CH3:30])[CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.B(F)(F)F.CCOCC.C(OCC)(=O)C>O1CCCC1.O>[Br:7][CH2:30][C:29](=[O:31])[CH:28]=[CH:27][C:20]1[CH:21]=[CH:22][C:23]([N+:24]([O-:26])=[O:25])=[C:18]([O:17][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:19]=1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8857Ethyl AcetateHCID 53975374HCID 53975374, compound

Product 1

HCID 54537144HCID 54537144, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pyridinium bromide perbromide (82.8 g) was added to a mixture of 1-(3-benzyloxy-4-nitrophenyl)but-1-en-3-one (70.0 g) and boron trifluoride etherate (290 ml) in tetrahydrofuran (1.4 l) under ice-cooling. The mixture was stirred for 2.5 hours at ambient temperature. The reaction mixture was added to a mixture of ethyl acetate and water under stirring. The separated organic layer was washed with saturated aqueous sodium bicarbonate and brine successively. The solution was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was recrystallized from diisopropyl ether to give 4-bromo-1-(3-benzyloxy-4-nitrophenyl)but-1-en-3-one (54.42 g).

Workup

  1. temperaturecooling
  2. stirringunder stirring
  3. washThe separated organic layer was washed with saturated aqueous sodium bicarbonate and brine successively
  4. dry with materialThe solution was dried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-15a48d267c6049a8a935537e24b178a9
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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