Potassium Hydroxide → 2-Amino-1-(4-bromophenyl)-1-ethanol

HRID 1160210Notes

Reaction equation

HRID 1160210 reaction equation
[BH4-].[Na+].[OH-].[K+].Cl.[NH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)=[O:9]>CO>[NH2:6][CH2:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)[OH:9]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 27982162-Amino-1-(4-bromophenyl)ethan-1-one hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 137289422-Amino-1-(4-bromophenyl)-1-ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Sodium borohydride (227 mg, 6.00 mmol) was dissolved in methanol (10 mL) and 5% potassium hydroxide in methanol (4.49 mL, 4.00 mmol) was carefully added. To this solution was added 2-Amino-1-(4-bromo-phenyl)-ethanone hydrochloride (1.0 g, 4.00 mmol) dissolved in methanol (10 mL) and stirring continued for 0.2 hours at room temperature. The mixture was concentrated, and quenched with saturated sodium bicarbonate (10 mL) and extracted with dichloromethane several times. The organics were combined, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The title compound was isolated as a yellow solid (677 mg, 77%). 1H NMR (300 MHz, CDCl3): 7.51-7.47 (d. 2H), 7.27-7.23 (d, 2H), 4.63-4.59 (m, 1H), 3.03 (dd, 1H), 2.76 (dd, 1H)

Workup

  1. concentrationThe mixture was concentrated
  2. customquenched with saturated sodium bicarbonate (10 mL)
  3. extractionextracted with dichloromethane several times
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d6385e3f14544f3fa1a967fe8d8cf8cb
Source dataset
uspto-grants-2010_10
Patent number
US07816354B2

Reaction notes

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