반응 #42221

반응 방정식

sodium hydroxide

9-borabicyclo[3.3.1]nonane

2-allyl-4-chloro-6-methoxyphenyl trifluoromethanesulfonate

potassium phosphate

hydrogen peroxide

→

6-chloro-4-methoxyindane

수율 68.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the reaction mixture was heated
2. 2
   온도at reflux for 20 h
3. 3
   기타The solvent was removed in vacuo
4. 4
   기타to provide a crude oil
5. 5
   기타Purification by flash column chromatography (silica, hexanes)

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.

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