Boron trifluoride → 7-Bromo-1-fluoronaphthalene

To a solution of BF3-etherate (0.86 ml, 1.25 M in THF, 6.5 mmol) in 12 ml dimethoxyethane was added at −5° C. a solution of 8-amino-2-bromo-naphthalene (1.20 g, 5.4 mmol) in dimethoxyethane (12 ml) over a periode of 35 min. After 1 hour a solution of tert-butylnitrite (0.62 ml, 5.4 mmol) in dimethoxyethane (24 ml) was added and the mixture was stirred for two hours at r.t. and the solvent was removed under reduced pressure. Chlorbenzene (120 ml) was added and the reaction mixture was refluxed for 50 min and the mixture was concentrated. The solid was diluted in methylene chloride and washed with NaHCO3. The organic phase was dried over MgSO4, filtered and reduced to give the crude product. Chromatography on silica gel (hexane) afforded 721 mg (59%) of the product as a brown oil. MS: m/e=242 (M+).

1. customthe solvent was removed under reduced pressure
2. additionChlorbenzene (120 ml) was added
3. temperaturethe reaction mixture was refluxed for 50 min
4. concentrationthe mixture was concentrated
5. additionThe solid was diluted in methylene chloride
6. washwashed with NaHCO3
7. dry with materialThe organic phase was dried over MgSO4
8. filtrationfiltered
9. customto give the crude product

ORD record

ord-8eaa7b289cad472f9668180d7981272a

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07005432B2