Ethyl Acetate → 1-(3-Bromo-4,5-dimethoxyphenyl)-1-ethanol

HRID 42976

Reaction equation

HRID 42976 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[CH:5]=[O:6].C[Mg+].[Br-].[CH3:17]COC(C)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH3:17])[CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 151736561-(3-Bromo-4,5-dimethoxyphenyl)-1-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under nitrogen, a solution of the 3-bromo-4,5-dimethoxybenzaldehyde (2.45 g; 10 mmol) in dry THF (10 ml) was added via syringe through a septum to a cold (ice-bath) solution of MeMgBr (15 mmol; 5.0 ml of 3.0 M Et2O solution) diluted with 10 ml dry THF. After the addition, the mixture was stirred for 10 minutes at 0° C., then for 1 hour at room temperatures. TLC (Hex:EtOAc=3:1) indicated complete disappearance of the reactant and a new product spot with lower Rf (0.25 vs 0.5).

Workup

  1. additionAfter the addition
  2. waitfor 1 hour at room temperatures

Sources & evidence

ORD record
ord-ceb391e5218e44e59e729defb587cafa
Source dataset
uspto-grants-2013_09
Patent number
US08536227B2

Linked notes

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