1-Bromoheptane → Heptylbenzene

A 30-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 0.358 g (2 mmol) of n-heptyl bromide, 0.476 g (2.4 mmol) of trimethoxyphenylsilane, 0.021 g (0.08 mmol) of palladium (II) bromide, 4.8 ml (4.8 mmol) of 1M tetrahydrofuran solution of tetra-n-butylammonium fluoride and 4.8 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.096 g (0.2 mmol) of di-tert-butylmethylphosphonium tetraphenylborate obtained in Example B-1 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 25° C. for 21 hours. After the completion of the reaction, 5 ml of toluene and 10 ml of saturated sodium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.300 g of 1-phenylheptane (yield: 85 mol % based on n-heptyl bromide). The identification of the product was made by mass spectroscopy.

1. customA 30-ml four-necked flask was equipped with a stirrer
2. additionadded into the flask
3. customThe flask was purged with argon
4. stirringby stirring at 25° C. for 21 hours
5. customAfter the completion of the reaction, 5 ml of toluene and 10 ml of saturated sodium chloride solution
6. additionwere added
7. customfollowed by separation
8. customThe organic phase was purified by column chromatography

ORD record

ord-c65cee3277e343ac81636a46664cd61d

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07728176B2