تفاعل #67687

معادلة التفاعل

1,2,3-tribromo-benzene

6,6-dimethylfulvene

n-butyllithium

ammonium chloride

→

desired product

المردود 66.0%

5-bromo-9-isopropylidene-1,4-dihydro-1,4-methano-naphthalene

المردود 66.0%

المذيبات

toluene

toluene

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with ethyl acetate
2. 2
   غسيلwashed with brine and water
3. 3
   تجفيفdried over sodium sulphate
4. 4
   أخرىevaporated
5. 5
   أخرىPurification of the crude material on silca gel in hexane

الإجراء التجريبي

To a stirred solution of 1,2,3-tribromo-benzene (4.34 g, 13.8 mmol) and 6,6-dimethylfulvene (2.38 g, assay 92.6%, 20.7 mmol) in dry toluene (60 ml) under a nitrogen atmosphere, 5.5 ml of a 2.5M toluene solution of n-butyllithium (14.5 mmol) were added dropwise at −5 to 0° C. within 10 minutes. After a further 10 minutes at 0° C. and 2 hours at ambient temperature, the reaction mixture was poured onto a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, washed with brine and water, dried over sodium sulphate and evaporated. Purification of the crude material on silca gel in hexane afforded 2.38 g of the desired product as a yellow oil (assay 84% by g.l.c., 55% yield). This reaction is also disclosed in WO 2007/068417.

المصدر