2,3-Dihydro-5-methoxy-1,1-dimethyl-1H-indene → HCID 23014065, compound

HRID 1350853Notes

Reaction equation

HRID 1350853 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6]2.ClCCl.B(Br)(Br)Br>ClCCl>[CH3:12][C:8]1([CH3:13])[C:9]2[C:5](=[CH:4][C:3]([OH:2])=[CH:11][CH:10]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 221522852,3-Dihydro-5-methoxy-1,1-dimethyl-1H-indeneHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 23014065HCID 23014065, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-methoxy-1,1-dimethylindane (941 mg, 5.34 mmol) in anhydrous dichloromethane (20 ml) was added 1.0 M boron tribromide dichloromethane solution (10.7 ml, 10.7 mmol) via a syringe at −78° C. The mixture was warmed to ambient temperature and stirred for 1.5 hours. The mixture was quenched with water (15 ml) and extracted with dichloromethane. The combined solution was washed with brine, dried over sodium sulfate. After filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give 878 mg of the crude 1,1-dimethylindan-5-ol as a gray solid.

Workup

  1. customThe mixture was quenched with water (15 ml)
  2. extractionextracted with dichloromethane
  3. washThe combined solution was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. customto separate solvent and sodium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f14d9b846dcc4df29719b9627ab33c71
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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