N-bromobutanimide → 5-bromo-6-methoxy-2,3-dihydro-1H-indene

HRID 874637Notes

Reaction equation

HRID 874637 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH2:15][CH2:14]2>C(#N)C.O>[Br:1][C:19]1[CH:18]=[C:17]2[C:13](=[CH:12][C:11]=1[O:10][CH3:9])[CH2:14][CH2:15][CH2:16]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 2281255-Methoxyindan

Product 1

HCID 152482825-bromo-6-methoxy-2,3-dihydro-1H-indeneYield 100.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

N-bromosuccinimide (1.26 g, 7.1 mmol) was added to a solution of 5-methoxyindan 124 (1.0 g, 6.7 mmol) in acetonitrile (34 mL). The resulting mixture was stirred at room temperature overnight. The mixture was diluted with water (100 mL) and extracted with dichloromethane (3×50 mL). The combined organic extracts were dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-10% ethyl acetate in hexane) provided 125 (1.53 g, 100%) as a liquid.

Workup

  1. extractionextracted with dichloromethane (3×50 mL)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-72cabfd5b4884feb8b4be0f6e6f0507a
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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