3-Bromo-2,5-dimethoxybenzaldehyde → 3-Bromo-2,5-dimethoxybenzyl Alcohol

HRID 1794491

Reaction equation

HRID 1794491 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1

Participants

4

Reactant 2

HCID 9310963-Bromo-2,5-dimethoxybenzaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 101927773-Bromo-2,5-dimethoxybenzyl AlcoholYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 51 (8.0 g, 33 mmol) in THF (100 ml) was added LiAlH4 (15 ml of 1.0M in THF) dropwise. After 15 min, the reaction was quenched with 2N HCl and the aqueous layer was extracted with EtOAc. The EtOAc layer was dried concentrated to give a solid (7.5 g, 93%): Mp=65–67° C.; 1H NMR (DMSO-d6) δ 7.05 (d, 1 H, J=3.0 Hz), 6.98 (d, 1 H, J=2.5 Hz), 5.28 (t, 1 H, J=4.9 Hz), 4.47 (d, 2 H, J=5.7 Hz), 3.73 (s, 3 H), 3.67 (s, 3 H); MS 245 (M−H)−

Workup

  1. customthe reaction was quenched with 2N HCl
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe EtOAc layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c37730fd665048269b860c83e468aef4
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Linked notes

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