Ethyl Acetate → 2-(3-Bromo-2-methoxyphenyl)ethanol

HRID 1474396Notes

Reaction equation

HRID 1474396 reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH2:8][C:9](OC)=[O:10])[CH:5]=[CH:6][CH:7]=1.[Li+].[BH4-].CCOC(C)=O>C1COCC1>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 66643982Methyl 2-(3-bromo-2-methoxyphenyl)acetate

Product 1

HCID 666440432-(3-Bromo-2-methoxyphenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl [3-bromo-2-(methyloxy)phenyl]acetate (8.20 g, 31.7 mmol) in 200 mL of dry THF under N2 at room temperature was added LiBH4 (32 mL, 63.32 mmol, 2M THF). After 1.5 hours, the reaction was warmed to reflux for 3 hours, and then cooled to room temperature. The solution was poured into EtOAc/1N HCl solution, and the layers were separated. The organic layer was washed with water, saturated Na2CO3 and brine, dried over anhydrous Na2SO4 and concentrated to give 2[3-bromo-2-(methyloxy)phenyl]ethanol

Workup

  1. temperaturethe reaction was warmed
  2. temperatureto reflux for 3 hours
  3. customthe layers were separated
  4. washThe organic layer was washed with water, saturated Na2CO3 and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-56e72e545ba348bab4ba8ac4c31953a0
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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