Methyl 2-bromo-4-methylbenzoate → 1-(2-Bromo-4-methylphenyl)cyclopentanol

HRID 1037112Notes

Reaction equation

HRID 1037112 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[Mg]([CH2:15][CH2:16][CH2:17][CH2:18][Mg]Br)Br>C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]1([OH:6])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 21779704Methyl 2-bromo-4-methylbenzoateHCID 178419681HCID 178419681, compound

Product 1

HCID 726983321-(2-Bromo-4-methylphenyl)cyclopentanolYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-bromo-4-methylbenzoate (5.0 g, 21.3 mmol) in THF (20 mL) was added dropwise BrMg(CH2)4MgBr (50 mL, 25.5 mmol) at 0° C. under nitrogen and then stirred at rt overnight. The reaction mixture was quenched with aqueous NH4Cl and extracted with EA. The combined organic layer was washed with aqueous NaHCO3 solution and brine, dried over Na2SO4. The solution was concentrated and the residue was purified by column chromatography over silica gel eluted with PE-EA (20:110:1) to provide 1-(2-bromo-4-methylphenyl)-cyclopentanol (4.2 g; yield 78%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.65 (d, 1 H), 7.39 (s, 1 H), 7.10 (d, 1 H), 4.84 (s, 1 H), 2.33 (s, 3 H), 1.89-1.74 (m, 8 H) ppm.

Workup

  1. customThe reaction mixture was quenched with aqueous NH4Cl
  2. extractionextracted with EA
  3. washThe combined organic layer was washed with aqueous NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe solution was concentrated
  6. customthe residue was purified by column chromatography over silica gel
  7. washeluted with PE-EA (20:110:1)

Sources & evidence

ORD record
ord-8b7fb9976eee497d965eb493f22d77a9
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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