1,2-Dibromoethane → 2-((10, 11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)methoxy)ethylbromide

To a solution of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-carboxaldehyde (11.3 g, 51 mmol, prepared in a similar way as described in Acta Chem. Scand. 1978, B33, 100-103) and tetrabutylammonium bromide (1.64 g, 5.1 mmol) in dichloromethane (100 ml) was added 1,2-dibromoethane (62 ml) and a 12 M sodium hydroxide solution (100 ml). The reaction mixture was stirred vigorously overnight and dichloromethane (100 ml) was added. The phases were separated and the aqueous phase was extracted with dichloromethane (100 ml). The combined organic phases were washed with a 0.2 M hydrochloric acid solution (100 ml), brine (25 ml) and dried over magnesium sulphate. The solvent was evaporated in vacuo to give 14.1 g of 2-((10, 11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)methoxy)ethylbromide. TLC: rf=0.48 (SiO2 ; ethyl acetate/n-heptane=1:4).

1. customThe phases were separated
2. extractionthe aqueous phase was extracted with dichloromethane (100 ml)
3. washThe combined organic phases were washed with a 0.2 M hydrochloric acid solution (100 ml), brine (25 ml)
4. dry with materialdried over magnesium sulphate
5. customThe solvent was evaporated in vacuo

ORD record

ord-5b933255bb2e4ecc9b11762a0e3f51a5

Source dataset

uspto-grants-1994_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05348965