Water → 1-(3-Bromo-4-methoxyphenyl)cyclopropanol

HRID 406395Notes

Reaction equation

HRID 406395 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[Br:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:9]([O:11]C)=O.C(OCC)(=O)C.O>C1COCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:5][C:6]1[CH:7]=[C:8]([C:9]2([OH:11])[CH2:2][CH2:1]2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 611662Methyl 3-bromo-4-methoxybenzoateHCID 178418443HCID 178418443, compound

Product 1

HCID 626698761-(3-Bromo-4-methoxyphenyl)cyclopropanol

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethylmagnesium bromide (3M solution in diethyl ether, 54.4 ml) was added at room temperature to a solution of methyl 3-bromo-4-methoxybenzoate (CAS No. 35450-37-4, 10 g) and titanium (IV) isopropoxide (23.9 ml) in THF (100 ml). The reaction mixture was stirred at room temperature overnight. Ethyl acetate and water were added to the reaction mixture and the precipitate was removed through Celite. The organic layer was separated, washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (7.77 g).

Workup

  1. customthe precipitate was removed through Celite
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ffa595b7212d474fb047107de8a57166
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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