2-BROMO-1,2,3,4-TETRAHYDRONAPHTHALEN-1-OL synthesis

8synthesis methods

Product Name:2-BROMO-1,2,3,4-TETRAHYDRONAPHTHALEN-1-OL
CAS Number:64245-04-1
Molecular formula:C10H11BrO
Molecular Weight:227.1

1056246-70-8 Synthesis

2-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

1056246-70-8
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2-BROMO-1,2,3,4-TETRAHYDRONAPHTHALEN-1-OL

64245-04-1
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Yield:64245-04-1 86%

Reaction Conditions:

with sodium tetrahydroborate in tetrahydrofuran;methanol at 0 - 20;Inert atmosphere;

Steps:

2-Bromo-1,2,3,4-tetrahydronaphthalen-1-ol

2-Bromo-3,4-dihydronaphthalen-1(2H)-one (4.50 g, 20.00 mmol, 1.00 equiv) was dissolved in a mixture of anhydrous MeOH and THF (1:2, 30 mL), set under an argon atmosphere and cooled to 0 °C. NaBH4 (0.53 g, 14.01 mmol, 0.70 equiv) was added in small portions. After complete addition the mixture was stirred at 0 °C for 15 min followed by stirring at room temperature until TLC indicated complete conversion of the starting material. The reaction mixture was poured onto water (100 mL) and extracted with Et2O (3 × 50 mL). The combined extracts were washed with sat. aq. NaCl solution (2 × 50 mL) and dried over Na2SO4. The solvent was evaporated and the residue recrystallized from hexanes under usage of active charcoal. The product was obtained as slightly ochre crystals. (3.89 g, 17.12 mmol, 86%)

References:

Grathwol, Christoph W.;W?ssner, Nathalie;Swyter, S?ren;Smith, Adam C.;Tapavicza, Enrico;Hofstetter, Robert K.;Bodtke, Anja;Jung, Manfred;Link, Andreas [Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 2170 - 2183] Location in patent:supporting information