Sulfuric Acid → HCID 22940227, compound

HRID 1766641Notes

Reaction equation

HRID 1766641 reaction equation
[CH2:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([OH:10])[C:4]=2[CH2:3][CH2:2]1.C(NC(C)C)(C)C.[Br:18]N1C(=O)CCC1=O.S(=O)(=O)(O)O>ClCCl>[Br:18][C:6]1[CH:7]=[CH:8][C:9]2[CH2:1][CH2:2][CH2:3][C:4]=2[C:5]=1[OH:10]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7912DiisopropylamineHCID 67184N-bromobutanimideHCID 742334-Hydroxyindan

Product 1

HCID 22940227HCID 22940227, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of indan-4-ol (24.2 g) in dichloromethane (200 mL) was added diisopropylamine (2.55 mL). To the solution was added N-bromosuccinimide (32.07 g) in small portions under ice-cooling, and the mixture was stirred at room temperature overnight. Diluted sulphuric acid (pH1, 200 mL) was added to the reaction mixture, and the mixture was separated. The organic layer was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1−1/1) to give the title compound (31.1 g).

Workup

  1. temperaturecooling
  2. customthe mixture was separated
  3. washThe organic layer was washed with water and brine successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1−1/1)

Sources & evidence

ORD record
ord-5e5ee6b4522f4d038bacb04223492a52
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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