Hydrochloric Acid → 3,3-Bis-(4-bromophenyl)prop-2-en-1-ol

A 1M solution of DIBAL-H in toluene (150 ml, 150 mmol) was added dropwise, at −70° C. over 30 min, to a stirred solution of 3,3-bis-(4-bromophenyl)-acrylic acid ethyl ester (24.5 g, 59.7 mmol) in dry THF (400 ml) and stirred for 30 min. The mixture was warmed to room temperature, and stirred for 1.5 h. The mixture was poured into 1N HCl (700 ml) with vigorous stirring and the product extracted with ethyl acetate (3×200 ml). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to give the crude product as an off-white solid, which was purified by column chromatography on silica gel (15% ethyl acetate in n-heptane eluent). The purified product was diluted in boiling heptane, filtered and the filtrate cooled, giving 15.8 g (72%) 3,3-bis-(4-bromophenyl)prop-2-en-1-ol as an crystalline solid.

1. stirringstirred for 1.5 h
2. stirringwith vigorous stirring
3. extractionthe product extracted with ethyl acetate (3×200 ml)
4. washThe combined organic extracts were washed with brine
5. dry with materialdried (MgSO4)
6. customevaporated
7. customto give the crude product as an off-white solid, which
8. customwas purified by column chromatography on silica gel (15% ethyl acetate in n-heptane eluent)
9. additionThe purified product was diluted
10. filtrationfiltered
11. temperaturethe filtrate cooled

ORD record

ord-a64b4843480143d59cb48ec2fddb43bb

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06869967B2