Реакция #42221

Уравнение реакции

sodium hydroxide

9-borabicyclo[3.3.1]nonane

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

potassium phosphate

hydrogen peroxide

→

6-chloro-4-methoxyindane

Выход 68.0%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture was heated
2. 2
   Температураat reflux for 20 h
3. 3
   ДругоеThe solvent was removed in vacuo
4. 4
   Другоеto provide a crude oil
5. 5
   ДругоеPurification by flash column chromatography (silica, hexanes)

Методика

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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