تفاعل #551203

معادلة التفاعل

triphenyl phosphine

1-bromo-4-chlorobenzene

3-buten-1-ol

→

title compound

المردود 52.0%

trans-4-(4'-Chlorophenyl)-3-buten-1-ol

المردود 52.0%

المذيبات

triethylamine

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىThe tube is sealed
2. 2
   درجة الحرارةheated 20 hr longer at 100°-120° C
3. 3
   درجة الحرارةThe mixture is cooled
4. 4
   أخرىpartitioned between 300 ml of 2N hydrochloric acid and ether
5. 5
   أخرىThe layers are separated
6. 6
   استخلاصthe aqueous layer is extracted with two additional volumes of ether
7. 7
   غسيلThe combined ether extracts are washed with 2×100 ml portions of 2N hydrochloric acid
8. 8
   تجفيفdried over sodium sulfate
9. 9
   استخلاصThe filtered ether extract
10. 10
    تركيزis concentrated under vacuum
11. 11
    أخرىto give 12.7 g of crude product which
12. 12
    أخرىis purified by chromatography on silica gel

الإجراء التجريبي

To a suspension of triphenyl phosphine (2.1 g, 8.0 mmole) in 300 ml of triethylamine and 30 ml of acetonitrile under nitrogen is added successively palladium (II) acetate (0.45 g, 2.0 mmole), 1-bromo-4-chlorobenzene (19.1 g, 110 mmole) and 3-buten-1-ol (7.21 g, 100 mmole) in a pressure tube. The tube is sealed and heated in an oil bath to 100° C. for 24 hr. The tube is opened under nitrogen, charged with additional palladium (II) acetate, resealed and heated 20 hr longer at 100°-120° C. The mixture is cooled, vented to nitrogen and partitioned between 300 ml of 2N hydrochloric acid and ether. The layers are separated and the aqueous layer is extracted with two additional volumes of ether. The combined ether extracts are washed with 2×100 ml portions of 2N hydrochloric acid and then dried over sodium sulfate. The filtered ether extract is concentrated under vacuum to give 12.7 g of crude product which is purified by chromatography on silica gel using toluene eluent. There is obtained 9.5 g of the title compound. Rf =0.77 (silica gel, toluene).

المصدر