Water → 1-[2-(Acetylamino)ethyl]-6-hydroxyindan

HRID 1978016Notes

Reaction equation

HRID 1978016 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16]C)[CH:14]=2)[CH2:9][CH2:8]1)(=[O:3])[CH3:2].B(Br)(Br)Br.O>ClCCl>[C:1]([NH:4][CH2:5][CH2:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:16])[CH:14]=2)[CH2:9][CH2:8]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 155239391-[2-(Acetylamino)ethyl]-6-methoxyindan

Product 1

HCID 219168881-[2-(Acetylamino)ethyl]-6-hydroxyindanYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[2-(acetylamino)ethyl]-6-methoxyindan (6.40 g, 27.4 mmol) in dichloromethane (150 ml) was added dropwise, under ice-cooling, boron tribromide (5.19 ml, 54.8 mmol). The mixture was then stirred for one hour. The reaction mixture was poured into water. The mixture was stirred for 8 hours at room temperature, which was subjected to extraction with chloroform. The extract solution was washed with brine, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was recrystallized from ethyl acetate/isopropyl ether to give 4.70 g (yield 78%) of the above-titled compound, m.p.107-108° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 8 hours at room temperature
  3. extractionwhich was subjected to extraction with chloroform
  4. washThe extract solution was washed with brine, which
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-628e5fe3c26947a291469c14e60c6528
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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