تفاعل #168984

معادلة التفاعل

5-isopropyl-6-methoxy-2,3-dihydro-benzo[1,4]dioxine

BBr3

→

5-isopropyl-6 hydroxy-2,3-dihydro-benzo[1,4]dioxine

المردود 65.4%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter 16 hours the solution was cooled to −78° C.
2. 2
   أخرىquenched with H2O
3. 3
   درجة الحرارةwarmed to room temperature
4. 4
   استخلاصextracted with CH2Cl2
5. 5
   غسيلThe combined organics were washed with brine
6. 6
   تجفيفdried over MgSO4
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىPurification via flash chromatography (7:3 hexane/ethyl acetate)

الإجراء التجريبي

To a solution of 5-isopropyl-6-methoxy-2,3-dihydro-benzo[1,4]dioxine (1.011 g, 4.9 mmol) in 15 ml CH2Cl2 at −78° C. was added BBr3 (7.3 ml, 7.3 mmol). The solution was allowed to warm to room temperature. After 16 hours the solution was cooled to −78° C., quenched with H2O, warmed to room temperature and extracted with CH2Cl2. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification via flash chromatography (7:3 hexane/ethyl acetate) afforded 5-isopropyl-6 hydroxy-2,3-dihydro-benzo[1,4]dioxine (0.622 g, 63%) as a pale yellow oil.

المصدر