4-BROMO-2-FLUOROBENZYL ALCOHOL synthesis
- Product Name:4-BROMO-2-FLUOROBENZYL ALCOHOL
- CAS Number:188582-62-9
- Molecular formula:C7H6BrFO
- Molecular Weight:205.02
112704-79-7
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$15.00/5 g
188582-62-9
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$12.00/5g
Yield: 86%
Reaction Conditions:
Stage #1:2-fluoro-4-bromobenzoic acid with borane in tetrahydrofuran at 0 - 85;
Stage #2: with hydrogenchloride in methanol;water at 25; for 2 h;
Steps:
(4-bromo-2-fluoro-phenyl)methanol (SI-8)
To a solution of commercially available 4-bromo-2-fluoro-benzoic acid (SI-7) (15 g, 68.5mmol) in THF (250 mL) was added BH3 (1.0 M in THF, 140 mL, 140 mmol) at 0 oC andthen the solution was stirred at 85 oC overnight. Then, the reaction was quenched withMeOH and 1 N HCl and stirred at room temperature for an additional 2 hours. The mixturewas extracted with EtOAc and the organic layer was washed with brine, dried overanhydrous Na2SO4, filtered and concentrated to give the crude product which was purifiedby column chromatography to obtain pure compound SI-8 (12 g, 86%) as a yellow oil. ESIMSm/z 205 [M+H]+ calc. for C7H6BrFO. This intermediate was used in the next stepwithout further characterization.
References:
Rabal, Obdulia;Sánchez-Arias, Juan A.;Cuadrado-Tejedor, Mar;de Miguel, Irene;Pérez-González, Marta;García-Barroso, Carolina;Ugarte, Ana;Estella-Hermoso de Mendoza, Ander;Sáez, Elena;Espelosin, Maria;Ursua, Susana;Haizhong, Tan;Wei, Wu;Musheng, Xu;Garcia-Osta, Ana;Oyarzabal, Julen [European Journal of Medicinal Chemistry,2018,vol. 150,p. 506 - 524] Location in patent:supporting information
57848-46-1
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188582-62-9
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179232-29-2
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188582-62-9
180 suppliers
$12.00/5g