Methyl 2-bromobenzoate → 2-(2-Bromophenyl)propan-2-ol

HRID 2265145Notes

Reaction equation

HRID 2265145 reaction equation
[CH3:1][Mg]Br.C([O:6][CH2:7][CH3:8])C.[Br:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1C(OC)=O.[Cl-].[NH4+]>O1CCCC1>[Br:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:7]([OH:6])([CH3:8])[CH3:1]

Participants

5

Reactant 3

HCID 11894Methyl 2-bromobenzoateHCID 25517Ammonium ChlorideHCID 178467822HCID 178467822, compound

Product 1

HCID 3295272-(2-Bromophenyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a nitrogen atmosphere, 49.5 mL of 3.0 M methylmagnesium bromide-diethyl ether solution was dropwise added to tetrahydrofuran (200 mL) solution of 10.7 g of methyl 2-bromobenzoate with cooling with ice. This was stirred at that temperature for 15 minutes, and then stirred at room temperature for 6 days. Aqueous saturated ammonium chloride solution was added to the reaction liquid, and extracted with diethyl ether. The diethyl ether layer was washed with saturated saline water, and then dried with anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through silica gel column chromatography (hexane/ethyl acetate=9/1) to obtain 7.4 g of the entitled compound.

Workup

  1. temperaturewith cooling with ice
  2. stirringstirred at room temperature for 6 days
  3. extractionextracted with diethyl ether
  4. washThe diethyl ether layer was washed with saturated saline water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was evaporated off under reduced pressure
  7. customthe residue was separated
  8. custompurified through silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-95344f1f52e44148bab5290b8468b3b7
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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