Triethylamine → (RS)-2-(2-bromo-ethyl)-1,2,3,4-tetrahydro-naphthalen-2-ol

To a 0° C. solution of triphenylphosphine (1.03 g, 3.93 mmol), in CH2Cl2 (15 ml) was added slowly a solution of bromine (0.192 ml, 3.74 mmol) in CH2Cl2. After 1 hour stirring at room temperature, the reaction mixture was cooled to 0° C. and treated slowly with a solution of (RS)-2-(2-hydroxy-ethyl)-1,2,3,4-tetrahydro-naphthalen-2-ol (0.72 g, 3.74 mmol) in CH2Cl2 (15 ml). After 1.5 hour stirring at room temperature, the reaction mixture was again cooled to 0° C., treated slowly with triethylamine (0.52 ml, 3.74 mmol), washed successively with H2O and brine, dried over Na2SO4, filtered and concentrated. The residue was chromatographed over silica gel (hexane-ethylacetate 9:1) to provide (RS)-2-(2-bromo-ethyl)-1,2,3,4-tetrahydro-naphthalen-2-ol (0.58 g, 61%) as a colorless oil, MS: m/e=255.1 (M).

1. temperaturethe reaction mixture was cooled to 0° C.
2. stirringAfter 1.5 hour stirring at room temperature
3. temperaturethe reaction mixture was again cooled to 0° C.
4. washwashed successively with H2O and brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was chromatographed over silica gel (hexane-ethylacetate 9:1)

ORD record

ord-e497cf153f0d4835a1ec64ec4bdca9a3

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06451819B2