Hydrogen Peroxide → 6-Chloro-4-methoxyindane

HRID 13943노트

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HRID 13943 반응식
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

참가 물질

8

반응물 5

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

생성물 1

HCID 685842676-Chloro-4-methoxyindane수율 68%

시약·촉매·용매 2

HCID 53485975CID 53485975촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3dbd0ecf65f24534a1576a5434116125
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728155B2

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