تفاعل #42221

معادلة التفاعل

sodium hydroxide

9-borabicyclo[3.3.1]nonane

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

potassium phosphate

hydrogen peroxide

→

6-chloro-4-methoxyindane

المردود 68.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was heated
2. 2
   درجة الحرارةat reflux for 20 h
3. 3
   أخرىThe solvent was removed in vacuo
4. 4
   أخرىto provide a crude oil
5. 5
   أخرىPurification by flash column chromatography (silica, hexanes)

الإجراء التجريبي

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.

المصدر