4-Aminophenethyl alcohol → HCID 54148235, compound

HRID 1711262Notes

Reaction equation

HRID 1711262 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.C1C(=O)N([Br:18])C(=O)C1>CN(C=O)C.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][C:3]=1[Br:18]

Participants

5

Reactant 2

HCID 669044-Aminophenethyl alcoholHCID 67184N-bromobutanimide

Product 1

HCID 54148235HCID 54148235, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-amino-phenyl)-ethanol (5.10 g, 37.2 mmol) in 37 mL of DMF was added NBS (6.60 g, 37.1 mmol) and the mixture stirred overnight at RT. The reaction was diluted with 100 mL of water and extracted with EtOAc (3×100 mL). The organic layer was washed with brine (200 mL) and dried over Na2SO4. The title compound was purified by silica gel flash chromatography eluting with 50% EtOAc/hexanes to give 5.10 g (64%) of a white solid. Mass spectrum (ESI, m/z): Calcd. for C8H10BrNO, 216.0 (M+H), found 216.1.

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. washThe organic layer was washed with brine (200 mL)
  3. dry with materialdried over Na2SO4
  4. customThe title compound was purified by silica gel flash chromatography
  5. washeluting with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-6b100a6a813b4a31a7515fec97c0da07
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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