Hydrogen Bromide → 6-chloro-2,3-dihydro-1H-inden-4-ol

HRID 13944Notes

Reaction equation

HRID 13944 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[C:4]([O:11]C)[CH:3]=1.Br>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 685842676-Chloro-4-methoxyindane

Product 1

HCID 685833386-chloro-2,3-dihydro-1H-inden-4-olYield 86.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To 6-chloro-4-methoxyindane (12.0 g, 0.072 mol) was added hydrogen bromide (30 wt. % in acetic acid, 325 mL) and the reaction mixture was stirred at 50° C. for 24 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (750 mL), washed with water (3×500 mL), saturated aqueous sodium bicarbonate (2×500 m/L), saturated aqueous sodium chloride (500 mL), dried (sodium sulfate) and the solvent was removed in vacuo to provide a brown oil. Purification by flash column chromatography (silica, dichloromethane) provided 10.5 g (80%) of 6-chloroindan-4-ol as a pale yellow solid. mp 56-59° C.; Anal. calcd. for C9H9ClO.0.2H2O: C, 62.77; H, 5.50. Found: C, 62.75; H, 5.26.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with water (3×500 mL), saturated aqueous sodium bicarbonate (2×500 m/L), saturated aqueous sodium chloride (500 mL)
  3. dry with materialdried (sodium sulfate)
  4. customthe solvent was removed in vacuo
  5. customto provide a brown oil
  6. customPurification by flash column chromatography (silica, dichloromethane)

Sources & evidence

ORD record
ord-529fbdb38afc404c9383629d14b0bef5
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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