Water → 2-Amino-5-bromobenzenemethanol

HRID 44189

Reaction equation

HRID 44189 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:9]=1[C:10](OC)=[O:11].O.[OH-].[Na+]>C1COCC1>[NH2:7][C:8]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:9]=1[CH2:10][OH:11]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 736224Methyl 2-amino-5-bromobenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 110308742-Amino-5-bromobenzenemethanolYield 59.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminium hydride (0.33 g, 8.7 mmol) in THF (10 ml) was added a solution of methyl 2-amino-5-bromobenzoate (2.0 g, 8.7 mmol) in 20 ml THF at 0° C. under nitrogen. Then stirring was continued for 2 h. 0.64 ml water, 2 M solution of sodium hydroxide (0.64 ml) and again 1.28 ml water were added before the resulting mixture was filtered through celite. Evaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1) yielded (2-amino-5-bromophenyl)methanol (1.0 g, 5.2 mmol, 59%) as off-white solid.

Workup

  1. filtrationwas filtered through celite
  2. customEvaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1)

Sources & evidence

ORD record
ord-eac0c260257f408f86bcc379c762a4e5
Source dataset
uspto-grants-2013_09
Patent number
US08541404B2

Linked notes

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