Sodium Hydroxide → HCID 57471187, compound

1-(4-chlorobenzyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine (13.18 g, 43.7 mmol, prepared analogously to 1-(3,4-dichlorobenzyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine cf. example 3) was dissolved in dichloromethane (200 mL). The solution was cooled to −10° C. and a 1 M solution of borontribromide in dichloromethane (131 mL, 131 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirring was continued for 2 h. The reaction mixture was poured on ice water and sodium hydroxide was added until pH 8 was reached. The aqueous layer was extracted with dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The crude product was used for the next step without further purification. Yield: 8.89 g (30.9 mmol, 71%, colorless solid).

1. temperatureto warm to room temperature
2. additionwas added until pH 8
3. extractionThe aqueous layer was extracted with dichloromethane
4. dry with materialThe combined organic extracts were dried (Na2SO4)
5. concentrationconcentrated in vacuo
6. customThe crude product was used for the next step without further purification

ORD record

ord-5249e8695aa4411aa961d27f21f25f7d

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067871B2