Hydrogen Peroxide → 6-Chloro-4-methoxyindane

HRID 13943Notes

Reaction equation

HRID 13943 reaction equation
C12BC(CCC1)CCC2.FC(F)(F)S(O[C:16]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([Cl:24])=[CH:18][C:17]=1[CH2:25][CH:26]=[CH2:27])(=O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[OH-].[Na+].OO>O1CCCC1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[Cl:24][C:19]1[CH:18]=[C:17]2[C:16]([CH2:27][CH2:26][CH2:25]2)=[C:21]([O:22][CH3:23])[CH:20]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 789669-Borabicyclo(3.3.1)nonaneHCID 865985572-Allyl-4-chloro-6-methoxyphenyl trifluoromethanesulfonate

Product 1

HCID 685842676-Chloro-4-methoxyindaneYield 68%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 9-borabicyclo[3.3.1]nonane (130 mL, 0.5 M in tetrahydrofuran) cooled to 0° C. was added 2-allyl-4-chloro-6-methoxyphenyl trifluoromethanesulfonate (16.5 g, 0.050 mol) in tetrahydrofuran (100 mL), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (1.5 g, 1.84 mmol), and potassium phosphate (16.0 g, 0.075 mol) and the reaction mixture was heated at reflux for 20 h. The reaction mixture was allowed to cool to room temperature and aqueous sodium hydroxide (2.5 N, 30 mL) was added followed by hydrogen peroxide (30 wt. %, 25 mL) and stirring was continued for 1 h. The solvent was removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, hexanes) provided 6.2 g (68%) of 6-chloro-4-methoxyindane as a white solid. mp 38-40° C.; Anal. calcd. for C10H11ClO: C, 65.76; H, 6.07. Found: C, 66.08; H, 6.11.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 20 h
  3. customThe solvent was removed in vacuo
  4. customto provide a crude oil
  5. customPurification by flash column chromatography (silica, hexanes)

Sources & evidence

ORD record
ord-3dbd0ecf65f24534a1576a5434116125
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

Loading…